Ethyl 3-(4-tert-butylphenyl)prop-2-enoate → Ethyl 3-(4-(tert-butyl)phenyl)propanoate

HRID 656309Notes

Reaction equation

HRID 656309 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=1)[CH3:2]>CO.CCOCC.[Pd]>[C:13]([C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:17])=[CH:12][CH:11]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 1

HCID 53424249Ethyl 3-(4-tert-butylphenyl)prop-2-enoate

Product 1

HCID 10728414Ethyl 3-(4-(tert-butyl)phenyl)propanoateYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The compound 34-2 (64 mg) according to the same procedure as described in Step 1 was dissolved in methanol (10 ml) and to the solution was added a catalytic amount of 10% palladium/carbon, followed by stirring at room temperature under hydrogen gas atmosphere for 2 hours. The resulting mixture was diluted with ether, filtered through celite, and then concentrated under reduced pressure to yield the compound 34-3 (60 mg, 93%)

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0583a8af4848448ca6b46493ffa3f5c9
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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