Dimethyl Ether → E-7-(4-hydroxyphenyl)hept-4-enoic acid

HRID 1060031Notes

Reaction equation

HRID 1060031 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10]/[CH:11]=[CH:12]/[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:5][CH:4]=1.COC.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10]/[CH:11]=[CH:12]/[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8254Dimethyl EtherHCID 25134Boron tribromide2×HCID 9921036E-7-(4-Methoxyphenyl)hept-4-enoic acid2×

Product 1

HCID 9899318E-7-(4-hydroxyphenyl)hept-4-enoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

E-7-(4-hydroxyphenyl)hept-4-enoic acid was prepared from E-7-(4-methoxyphenyl)hept-4-enoic acid by removal of the methyl ether with boron tribromide. Boron tribromide was added to a solution of E-7-(4-methoxyphenyl)hept-4-enoic acid in methylene chloride at −78° C. and stirred for four hours. The product, E-7-(4-hydroxyphenyl)hept-4-enoic acid, was obtained by aqueous work-up of the reaction mixture followed by chromatography on silica gel, and was fully characterized by spectroscopic methods (infrared and nuclear magnetic resonance) and combustion analysis.

Sources & evidence

ORD record
ord-c95e9ac11b094f129df9081f0fb4efcf
Source dataset
uspto-grants-2003_02
Patent number
US06521664B1

Reaction notes

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