Diphenylmethyl 4-(ethyl acetoxy)-3,5-dimethoxybenzoate → 4-(Ethyl acetoxy)-3,5-dimethoxybenzoic acid

HRID 2269888Notes

Reaction equation

HRID 2269888 reaction equation
[CH2:1]([CH2:3][C:4]([O:6][C:7]1[C:28]([O:29][CH3:30])=[CH:27][C:10]([C:11]([O:13]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:12])=[CH:9][C:8]=1[O:31][CH3:32])=[O:5])[CH3:2]>[Pd].C(O)C.C(OCC)(=O)C.ClCCl>[CH2:1]([CH2:3][C:4]([O:6][C:7]1[C:28]([O:29][CH3:30])=[CH:27][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[O:31][CH3:32])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 53724741Diphenylmethyl 4-(ethyl acetoxy)-3,5-dimethoxybenzoate

Product 1

HCID 544423524-(Ethyl acetoxy)-3,5-dimethoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22027680Ethanol ethyl acetate methylene chlorideSolvent

Procedure

Combine diphenylmethyl 4-(ethyl acetoxy)-3,5-dimethoxybenzoate (4.3 g, 9.56 mmol), 5% palladium-on-carbon (0.5 g), and ethanol/ethyl acetate/dichloromethane (200 mL/15 mL/15 mL). Hydrogenate at an initial pressure of 55 psi in a Parr apparatus. After 16 hours, filter and concentrate the filtrate to give a residue. Recrystallize the residue from diethyl ether/hexane to give the title compound: Rf=0.35 (silica gel, 6% methanol/dichloromethane).

Workup

  1. filtrationfilter
  2. concentrationconcentrate the filtrate
  3. customto give a residue
  4. customRecrystallize the residue from diethyl ether/hexane

Sources & evidence

ORD record
ord-e573ed72c61346bb9541f7f530b5a125
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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