Benzyl Alcohol → Benzyl 4-bromo-2-methylbenzoate

HRID 844709Notes

Reaction equation

HRID 844709 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1>O=S(Cl)Cl>[Br:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([O:6][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:5])=[C:2]([CH3:1])[CH:10]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22568915Benzyl 4-bromo-2-methylbenzoateYield 80%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

Using General Esterification Method C; 2-methyl-4-bromo-benzoic acid (2.15 g, 10.0 mmols) was refluxed for 3 h with 10 mL SOCl2. The resulting solution concentrated under reduced pressure and the crude acyl chloride was combined with benzyl alcohol (1.08 g, 10.0 mmols) and pyridine (1.6 mL, 20.0 mmols) to give the title compound (2.4 g, 80%) after work-up and column chromatography (2-5% EtOAc-hexanes) as a colorless oil.

Workup

  1. concentrationThe resulting solution concentrated under reduced pressure

Sources & evidence

ORD record
ord-0388353bf8f74873b3cf7c306a13927a
Source dataset
uspto-grants-2002_04
Patent number
US06380256B1

Reaction notes

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