3-Benzyloxy-5-isobutylbenzoic acid methyl ester → 3-Hydroxy-5-isobutylbenzoic acid methyl ester

HRID 1430996Notes

Reaction equation

HRID 1430996 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([CH2:10][CH:11]([CH3:13])[CH3:12])[CH:7]=[C:6]([O:14]CC2C=CC=CC=2)[CH:5]=1>C(O)C.[OH-].[Pd+2].[OH-]>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([CH2:10][CH:11]([CH3:13])[CH3:12])[CH:7]=[C:6]([OH:14])[CH:5]=1

Participants

4

Reactant 1

HCID 585288613-Benzyloxy-5-isobutylbenzoic acid methyl ester

Product 1

HCID 585288773-Hydroxy-5-isobutylbenzoic acid methyl esterYield 100.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-benzyloxy-5-isobutylbenzoic acid methyl ester (388 mg, 1.30 mmol) in ethanol (20 mL) was added palladium hydroxide (80 mg, 20 wt % on carbon). After shaking on Parr hydrogenation apparatus for 3 h at 45 psi, the catalyst was filtered through a pad of Celite and the solvent evaporated to afford 271 mg (100%) of 3-hydroxy-5-isobutylbenzoic acid methyl ester. 1H NMR (300 MHz. DMSO-d6) δ 0.850 (d, 6H, J=6 Hz), 1.77-1.84 (m, 1H), 2.42 (d, 2H, J=7 Hz). 3.81 (s, 3H), 6.81-6.82 (m, 1H), 7.17-7.19 (m, 2H), 9.70 (s, 1H).

Workup

  1. filtrationthe catalyst was filtered through a pad of Celite
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-24de5030cd414e389e2828e1c6e49a33
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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