Benzyl 6-hydroxy-6-(4,4-dimethyl-2,6-dioxocyclohexylidene)-hexanoate → 6-Hydroxy-6-(4,4-dimethyl-2,6-dioxocyclohexylidene)-hexanoic acid

HRID 2086382Notes

Reaction equation

HRID 2086382 reaction equation
[OH:1][C:2](=[C:17]1[C:22](=[O:23])[CH2:21][C:20]([CH3:25])([CH3:24])[CH2:19][C:18]1=[O:26])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9]CC1C=CC=CC=1)=[O:8]>CO.[Pd]>[OH:1][C:2](=[C:17]1[C:18](=[O:26])[CH2:19][C:20]([CH3:24])([CH3:25])[CH2:21][C:22]1=[O:23])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 22728382Benzyl 6-hydroxy-6-(4,4-dimethyl-2,6-dioxocyclohexylidene)-hexanoate

Product 1

HCID 227283796-Hydroxy-6-(4,4-dimethyl-2,6-dioxocyclohexylidene)-hexanoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 6-hydroxy-6-(4,4-dimethyl-2,6-dioxocyclohexylidene)-hexanoate (1.50 g, 4.19 mmol) was hydrogenated over Pd/C (10%) (150 mg) in MeOH (20 ml) at room temperature for 10 hours. The catalyst was filtered off, and the filtrate was evaporated, yielding 6-hydroxy-6-(4,4-dimethyl-2,6-dioxocyclohexylidene)-hexanoic acid (1.10 g, 98%);

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-2fb380eaee0d4da298e5bfd459d7307d
Source dataset
uspto-grants-2004_04
Patent number
US06723843B2

Reaction notes

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