HCID 59556611, compound → 4-(2-tert-Butoxy-2-oxoethoxy)benzoic acid

HRID 1172926Notes

Reaction equation

HRID 1172926 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][O:8][C:9]1[CH:24]=[CH:23][C:12]([C:13]([O:15]CC2C=CC=CC=2)=[O:14])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:25])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:23][CH:24]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59556611HCID 59556611, compound

Product 1

HCID 211804184-(2-tert-Butoxy-2-oxoethoxy)benzoic acidYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 500 mL high-pressure flask was charged with benzyl 4-(2-tert-butoxy-2-oxoethoxy)benzoate (2.06 g, 6.02 mmol) in methanol (100 ml). Palladium on carbon (0.320 g, 0.301 mmol) was added, the resulting suspension was allowed to shake under an atmosphere of hydrogen (47 Psi) at room temperature for 6 h. The mixture was filtered through Celite®), the colorless filtrate was concentrated to afford 4-(2-tert-butoxy-2-oxoethoxy)benzoic acid (1.5 g, 5.95 mmol, 99% yield) as pale yellow solid. LC/MS (Table 1, Method a) Rt=3.03 min.; MS m/z: 251.30 (M−H)−. 1H NMR (400 MHz, Solvent d-DMSO) ppm 7.88 (d, J=8.99 Hz, 2H), 6.98 (d, J=9.00 Hz, 2H), 4.75 (s, 2H), 1.43 (s, 9H).

Workup

  1. filtrationThe mixture was filtered through Celite®), the colorless filtrate
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-3a9fac745cec47a6ac520865dd4ec434
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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