Benzyl Alcohol → Benzyl 4-bromo-2-methylbenzoate

HRID 1596946Notes

Reaction equation

HRID 1596946 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-854b1d8028b94bb991885fdb65a124cf
Source dataset
uspto-grants-2001_09
Patent number
US06291677B1

Reaction notes

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