HCID 53838810, compound → HCID 54254145, compound

HRID 1170041Notes

Reaction equation

HRID 1170041 reaction equation
[C:1]([O:5][C:6](=[O:23])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=1[O:15]CC1C=CC=CC=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:23])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=1[OH:15])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 53838810HCID 53838810, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54254145HCID 54254145, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of [4-methyl-2-(phenylmethoxy)phenyl]acetic acid tert-butyl ester (10.67 g, 34.2 mmol) in 125 ml of ethanol was added palladium black (200 mg), the mixture was hydrogenated (using a hydrogen balloon) at 30° C. for 10 hr. After the starting material disappeared completely (detected by TLC), the solid was filtered off, and the solvent was evaporated to give a crude product of (2-hydroxy-4-methylphenyl)acetic acid tert-butyl ester, 7.32 g (96%) as white solid. 1H NMR (CDCl3) δ: 7.931 (1H, s, br), 6.955 (1H, d, J=7.56 Hz), 6.799 (1H, s), 6.688 (1H, d, J=7.81 Hz), 3.551(2H, S), 2.299 (3H, s), 1.472 (9H, s) ppm.

Workup

  1. customat 30° C.
  2. customfor 10 hr
  3. filtrationthe solid was filtered off
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-baaabd2d6dbc4299a0f2c8de1d2ceae0
Source dataset
uspto-grants-2010_11
Patent number
US07825216B2

Reaction notes

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