Benzyl Alcohol → Benzyl 4-bromo-2-methylbenzoate

HRID 2185287Notes

Reaction equation

HRID 2185287 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-370c46180b8146e48d8d6f474ba5fd08
Source dataset
uspto-grants-2002_06
Patent number
US06399774B1

Reaction notes

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