2-(3-Methoxyphenyl)propanoic acid → 2-(3-Hydroxyphenyl)propionic acid, (+-)-

HRID 885257Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]([CH:9]([CH3:13])[C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1>Br.C(O)(=O)C>[OH:2][C:3]1[CH:4]=[C:5]([CH:9]([CH3:13])[C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-(3-Methoxy-phenyl)-propionic acid (0.1 g, 0.55 mmol) was dissolved in a mixture of hydrogen bromide (2 mL) and acetic acid (2 mL) and heated to 100° C. overnight. The mixture was partitioned between H2O and EtOAc, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated to give the desired product.

Workup

customThe mixture was partitioned between H2O and EtOAc
extractionthe aqueous layer was extracted with EtOAc
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-009e52aca744482aaee07a56988fc909
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242145B2

Reaction notes

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