Menthol → Methyl 2-(4-bromophenyl)acetate

HRID 1501252Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH:16]1(C)CCC(C(C)C)C(O)C1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:16])=[O:10])=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 1254Menthol

HCID 24386Thionyl Chloride

HCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 316783Methyl 2-(4-bromophenyl)acetateYield 99.8%

Procedure

To a solution of 2-(4-bromophenyl)acetic acid (10 g, 46.7 mmol) in menthol was added thionyl chloride (8.34 g, 70.07 mmol) dropwise. The mixture was then stirred at room temperature for 18 hours. The reaction mixture was concentrated, and obtained methyl 2-(4-bromophenyl)acetate (10.5 g, 99.8%).

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-288fa4685a594942b3a075c8373571ef
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206128B2

Reaction notes

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