HCID 23375, compound → 4,4-Dimethylpentanoic acid

HRID 1912061Notes

Reaction equation

HRID 1912061 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[CH:3]=[CH:4][C:5]([OH:7])=[O:6].CO.O1CCCC1>[Pd].C(O)C>[CH3:1][C:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 23375HCID 23375, compoundHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 142374,4-Dimethylpentanoic acidYield 101.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4,4-Dimethyl-2-pentenoic acid (343 g), methanol/tetrahydrofuran=3/1 (150 mL) and ethanol (1240 mL) were mixed. After an addition of 10 w/w % palladium on activated carbon (31 g) to the mixture, the mixture was stirred at RT for 10.5 hr under hydrogen atmosphere (1 atm). The 10 w/w % palladium on activated carbon was filtered off and the filtrate was concentrated in vacuo to give the title compound (354 g) as a crude product.

Workup

  1. filtrationThe 10 w/w % palladium on activated carbon was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d33416b87f1148b5af0e8c2ff78f69bd
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

Loading…