HCID 68058524, compound → HCID 68058523, compound

HRID 1035689Notes

Reaction equation

HRID 1035689 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][C:11](=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.[Pd]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 68058524HCID 68058524, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68058523HCID 68058523, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6.646 g of ethyl [4-(4-hydroxyphenyl)cyclohexylidene]acetate (26.53 mmol, 1 eq.) are placed in 150 mL of ethyl acetate in a Parr bottle under nitrogen. 0.77 g of 10% palladium-on-charcoal (0.72 mmol, 0.03 eq.) is added and the reaction medium is placed under 50 psi of hydrogen for 3 hours at 25° C. The reaction medium is filtered and concentrated to give 6.27 g of ethyl [4-(4-hydroxyphenyl)cyclohexyl]acetate.

Workup

  1. filtrationThe reaction medium is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-fdc282ceee2742588ae9c960a91ea86d
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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