Benzeneacetic acid, 4-hydroxy-, methyl ester → HCID 178500704, compound

HRID 1670663Notes

Reaction equation

HRID 1670663 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1>CO.[Rh]>[OH:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 178500704HCID 178500704, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 4-hydroxyphenylacetate (10.01 g, 60.2 mmol, CAS 14199-15-6), rhodium (5% on Alumina) (0.073 g, 0.71 mmol) in MeOH (30 mL) was hydrogenated at 8 bar. The crude was filtered through Celite and concentrated at reduced pressure. The remaining colorless oil was dissolved in isohexane and EtOAc and purified by flash chromatography using EtOAc (20-50%) in isohexane to afford the title cis compound (4.31 g, 42%) as colorless oil. NMR analysis of both trans and cis isomers were compared to make sure that the right isomer was used in subsequent steps.

Workup

  1. filtrationThe crude was filtered through Celite
  2. concentrationconcentrated at reduced pressure
  3. dissolutionThe remaining colorless oil was dissolved in isohexane
  4. customEtOAc and purified by flash chromatography

Sources & evidence

ORD record
ord-ac5dd49f12eb49678d72f5055f8689f4
Source dataset
uspto-grants-2011_08
Patent number
US07994179B2

Reaction notes

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