HCID 69268623, compound → α-Butyl-α-methylbenzeneacetic acid

HRID 494509Notes

Reaction equation

HRID 494509 reaction equation
[CH3:1][C:2]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH2:13]/[CH:14]=[CH:15]/[CH3:16])[C:3]([O:5]CC1C=CC=CC=1)=[O:4]>C(OCC)(=O)C.[Pd]>[CH3:1][C:2]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([CH2:13][CH2:14][CH2:15][CH3:16])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 1

HCID 69268623HCID 69268623, compound

Product 1

HCID 15472787α-Butyl-α-methylbenzeneacetic acidYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 27A (2.45 g, 8.32 mmol) in ethyl acetate (20 mL) was treated with 10% palladium on carbon (0.245 g, 10 weight percent) and stirred under a hydrogen balloon for 72 hours. The vessel was purged with nitrogen gas and the mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo to give the title compound (1.71 g, 99%). 1H NMR (300 MHz, CDCl3): δ ppm 0.87 (m, 3 H) 1.24 (m, 4 H) 1.57 (m, 3H) 1.98 (m, 2 H) 7.32 (m, 5 H). MS (DCI NH3+) m/z 224 (M+NH4)+.

Workup

  1. customThe vessel was purged with nitrogen gas
  2. filtrationthe mixture was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-754966c3f2ba475b9658638dd4758199
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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