Benzyl alcohol

Cat.NO.:A194236 Purity:98%

Product Details of Benzyl alcohol

CAS No. :	100-51-6
Formula :	C₇H₈O
M.W :	108.14
SMILES Code :	OCC1=CC=CC=C1
Synonyms :	Benzenemethanol
MDL No. :	MFCD00004599
InChI Key :	WVDDGKGOMKODPV-UHFFFAOYSA-N
Pubchem ID :	244

Safety of Benzyl alcohol

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Benzyl alcohol

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 100-51-6 ]
Downstream synthetic route of [ 100-51-6 ]

[ 100-51-6 ] Synthesis Path-Upstream 1~14

1
[ 7379-35-3 ]
[ 100-51-6 ]
[ 49826-70-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 5℃; for 0.25 h; Stage #2: at 5 – 60℃;	A flask is charged with NaH (60percent dispersion in mineral oil, 0.72 g, 18.0 mmol) then suspended in DMF (30 mL) and cooled to 5° C. To this mixture is added benzyl alcohol (1.04 mL, 10.0 mmol) drop-wise. The mixture is stirred for 15 minutes then 4-chloropyridine-HCl (1.00 g, 6.67 mmol) is added in three portions over 5 min. The resulting mixture is stirred at 5° C. for 10 min then warmed to 60° C. and stirred for 1.5 h. The mixture is then cooled to 23° C., treated with water, and extracted with EtOAc. The combined organics are dried with MgSO₄, filtered, and concentrated in vacuo. Purification of the crude by flash chromatography (SiO₂, 5percent EtOAc in hexanes to 50percent EtOAc in hexanes) gives the title intermediate (1.10 g, 89percent).
89%	Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 5℃; for 0.25 h; Stage #2: at 5 – 60℃; for 1.75 h;	Example 3 Synthesis of 4-(benzyloxy)pyridine. A flask is charged with NaH (60percent dispersion in mineral oil, 0.72 g, 18.0 mmol) then suspended in DMF (30 mL) and cooled to 5 °C. To this mixture is added benzyl alcohol (1.04 mL, 10.0 mmol) drop-wise. The mixture is stirred for 15 minutes then 4-chloropyridine-HCl (1.00 g, 6.67 mmol) is added in three portions over 5 min. The resulting mixture is stirred at 5 °C for 10 min then warmed to 60 °C and stirred for 1.5 h. The mixture is then cooled to 23 °C, treated with water, and extracted with EtOAc. The combined organics are dried with MgSO₄, filtered, and concentrated in vacuo. Purification of the crude by flash chromatography (SiO₂, 5percent EtOAc in hexanes to 50percent EtOAc in hexanes) gives the title intermediate (1.10 g, 89percent).

References:

[1] Journal of Organic Chemistry, 2017, vol. 82, # 24, p. 13756 – 13767.

[2] Patent: US2011/275627, 2011, A1, . Location in patent: Page/Page column 60.

[3] Patent: EP2331541, 2011, A1, . Location in patent: Paragraph 0070; 0071.

2
[ 626-61-9 ]
[ 100-51-6 ]
[ 49826-70-2 ]

References:

[1] Tetrahedron, 1987, vol. 43, # 11, p. 2557 – 2564.

[2] Patent: WO2010/90716, 2010, A1, . Location in patent: Page/Page column 301.

3
[ 15854-87-2 ]
[ 100-51-6 ]
[ 49826-70-2 ]

References:

[1] Tetrahedron, 2002, vol. 58, # 24, p. 4931 – 4935.

4
[ 186519-89-1 ]
[ 100-51-6 ]
[ 16019-34-4 ]

References:

[1] Tetrahedron Letters, 1998, vol. 39, # 32, p. 5685 – 5688.

5
[ 132433-56-8 ]
[ 100-51-6 ]
[ 94777-00-1 ]
[ 26364-65-8 ]

References:

[1] Heterocycles, 1996, vol. 42, # 1, p. 265 – 272.

6
[ 160314-52-3 ]
[ 100-51-6 ]
[ 27591-56-6 ]
[ 26364-65-8 ]

References:

[1] Journal of the Chemical Society, Chemical Communications, 1994, # 19, p. 2301 – 2302.

7
[ 73330-93-5 ]
[ 100-51-6 ]
[ 13105-53-8 ]

References:

[1] Synthetic Communications, 2004, vol. 34, # 1, p. 33 – 39.

8
[ 111-36-4 ]
[ 100-51-6 ]
[ 13105-53-8 ]

References:

[1] Synthesis, 2008, # 10, p. 1612 – 1618.

9
[ 292638-85-8 ]
[ 100-51-6 ]
[ 4126-60-7 ]

References:

[1] Journal of Organic Chemistry, 1992, vol. 57, # 15, p. 4243 – 4249.

[2] Patent: WO2004/31156, 2004, A1, . Location in patent: Page 30.

[3] Patent: US2005/54707, 2005, A1, . Location in patent: Page/Page column 12.

10
[ 2935-35-5 ]
[ 100-51-6 ]
[ 10419-67-7 ]

References:

[1] Organometallics, 2014, vol. 33, # 16, p. 4269 – 4278.

11
[ 56-84-8 ]
[ 100-51-6 ]
[ 6327-59-9 ]

References:

[1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 17, p. 6220 – 6229.

12
[ 100-51-6 ]
[ 191348-16-0 ]

References:

[1] Organic Letters, 2012, vol. 14, # 5, p. 1206 – 1209.

13
[ 100-51-6 ]
[ 105891-54-1 ]

References:

[1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 44, p. 8537 – 8545.

14
[ 100-51-6 ]
[ 477889-91-1 ]
[ 1083329-33-2 ]

References:

[1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 – 9333.

[2] Organic and Biomolecular Chemistry, 2009, vol. 7, # 24, p. 5103 – 5112.

[ 100-51-6 ] Synthesis Path-Downstream 1~35

1
[ 1122-12-9 ]
[ 100-51-6 ]
[ 55052-04-5 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1974,p. 2092 – 2095.

2
[ 4016-63-1 ]
[ 100-51-6 ]
[ 3868-36-8 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1194 – 1198.
[2]Tetrahedron Letters,2011,vol. 52,p. 2176 – 2180.

3
[ 6168-83-8 ]
[ 100-51-6 ]
[ 127604-17-5 ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 2043 – 2066.

4
[ 17356-08-0 ]
[ 100-51-6 ]
[ 538-28-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2827 – 2830.

5
[ 4760-34-3 ]
[ 100-51-6 ]
[ 2622-63-1 ]

References: [1]Synlett,2004,p. 1628 – 1630.

6
[ 32161-30-1 ]
[ 104-15-4 ]
[ 100-51-6 ]
benzyl m,p-dimethoxy-L-phenylalaninate p-toluenesulfonic acid salt [ No CAS ]

References: [1]Organic Letters,2006,vol. 8,p. 1921 – 1924.

7
[ 16957-70-3 ]
[ 100-51-6 ]
benzyl trans-2-methyl-2-pentenoate [ No CAS ]

References: [1]Journal of the American Chemical Society,2001,vol. 123,p. 6445 – 6446.

8
[ 100-51-6 ]
(+-)-6-methyl-2-oxo-tetrahydro-pyran-3-carbaldehyde [ No CAS ]
[ 538-28-3 ]

References: [1]Journal of Pharmaceutical Sciences,1984,vol. 73,p. 374 – 377.

9
[ 34846-90-7 ]
[ 100-51-6 ]
[ 188569-98-4 ]

References: [1]Patent: JP2005/170912,2005,A .Location in patent: Page/Page column 7.

10
[ 38573-88-5 ]
[ 100-51-6 ]
[ 295376-29-3 ]
[ 1036724-55-6 ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 4588 – 4590.

11
[ 55453-87-7 ]
[ 100-51-6 ]
[ 60548-16-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	toluene-4-sulfonic acid; In toluene;Reflux;	10 g (0.037 moles) of 6,11-dihydro-11-oxodibenz[b,e] oxepin-2-acetic acid were dissolved in 100 ml of toluene and 2 g (0.01 moles) of p-toluenesulfonic acid (p-TsOH) and 17.5 ml (0.169 moles) of benzyl alcohol were added to this solution. The reaction was equipped with a Dean-Stark, a mixture of water/toluene thus being distilled. The reaction was maintained until 0.7 ml of water were collected. The reaction was left to cool to 20-25°C, at which temperature 1.5 ml (0.011 moles) of Et3N were added. The resulting solution was concentrated under reduced pressure until obtaining a residue which was dissolved in isopropanol (50 ml), giving rise to a suspension. The obtained suspension was stirred at 20-25°C for 30 minutes, then being cooled at 0-5°C. Stirring was maintained at this temperature for 30 minutes. Then, the suspension was filtered and washed, obtaining 12.5 g (0.036 moles, 98percent) of a white solid identified as the compound of the title, the spectroscopic properties of which are: 1H-NMR (CDCl3, 400 MHz), delta: 3.70 (s, 2H); 5.14 (m, 4H), 7.02 (d, 1H), 7.33 (m, 1H); 7.41-7.46 (m, 4H), 7.52 (m, 3H); 7.88 (m, 2H); 8.15 (d, 1H) ppm. 13C-NMR (CDCl3, 400 MHz), delta: 39.95; 66.56; 73.37; 120.88; 124.92; 127.48; 127.64; 128.04 (2); 128.10; 128.39 (2); 129.05; 129.25; 132.32; 132.58; 135.33;135.53; 136.20; 140.60; 160.72; 171.48; 191.01. MS, M++1: 358.12.

References: [1]Patent: EP2145882,2010,A1 .Location in patent: Page/Page column 13.

12
[ 4016-63-1 ]
[ 100-51-6 ]
[ 3868-37-9 ]

References: [1]Tetrahedron Letters,2011,vol. 52,p. 2176 – 2180.

13
[ 5900-59-4 ]
[ 100-51-6 ]
[ 7012-94-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium hydroxide; In toluene; at 90℃; for 20h;	General procedure: To an oven-dried 20 cm3 test tube with a ground-in stopperequipped with a stir bar were added anthranilamide (1.0 mmol), benzyl alcohol (1.0 mmol), KOH (2.0 mmol),and 4 cm3 toluene. The test tube was put in an oil bath potpreheated at 90 C and the mixture was stirred for 20 h at90 C. After cooling to room temperature, the rea Details Products CAS 37-87-6 Read more Products CAS 56-36-0 Read more Products CAS 56-59-7 Read more Reviews There are no reviews yet. Be the first to review “Benzyl alcohol” Cancel reply Your email address will not be published. Required fields are marked * Your rating * Your review * Name * Email * Save my name, email, and website in this browser for the next time I comment. Previous Ethyl 1-ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate Next 1,2,3,4,5,6-Hexakis[2-(trimethylsilyl)ethynyl]benzene Easy CDMO Easy CDMO is China TOP100 CDMO company. We believe: Easy CDMO, Medicinal Chemical is Big. More than 100 scientists are serving you. Quick Links About Us Products Blog Contacts Support Links Privacy Policy Term And Condition Locations Office address: Chenxun Technology Building, No. 633, Jinzhong Road, Changning District, Shanghai info@easycdmo.com +8602161734564 © Copyright Easy CDMO 2025. All Rights Reserved.

Products

Product Details of Benzyl alcohol

Safety of Benzyl alcohol

Application In Synthesis of Benzyl alcohol

[ 100-51-6 ] Synthesis Path-Upstream 1~14

[ 100-51-6 ] Synthesis Path-Downstream 1~35

Details

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Ethyl 1-ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

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