Benzyl 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoate → 4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoic acid

HRID 654219Notes

Reaction equation

HRID 654219 reaction equation
[CH3:1][C:2]1([CH3:33])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([O:16][C:17]3[CH:32]=[CH:31][C:20]([C:21]([O:23]CC4C=CC=CC=4)=[O:22])=[CH:19][CH:18]=3)=[O:15])[CH:5]=[CH:4][C:3]1=2>[Pd].C(OCC)(=O)C>[CH3:1][C:2]1([CH3:33])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]([O:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:31][CH:32]=3)=[O:15])[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 1

HCID 19748013Benzyl 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoate

Product 1

HCID 98633134-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 150 mg (0.3394 mmol) of benzyl 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoate and 50 mg of 10% palladium on carbon in 5 ml of ethyl acetate was stirred under a hydrogen atmosphere at room temperature for 4 hours. The reaction mixture was then filtered and the filtrate was concentrated in-vacuo. The residue was dissolved in ether and extracted with aqueous NaOH solution. The aqueous extract was then acidified with glacial acetic acid and extracted with ether. The ether extract was washed with saturated NaCl solution and then concentrated in-vacuo. The resultant residue was recrystallized from ethyl acetate to give the title compound as a white solid.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate was concentrated in-vacuo
  3. dissolutionThe residue was dissolved in ether
  4. extractionextracted with aqueous NaOH solution
  5. extractionThe aqueous extract
  6. extractionextracted with ether
  7. extractionThe ether extract
  8. washwas washed with saturated NaCl solution
  9. concentrationconcentrated in-vacuo
  10. customThe resultant residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7e8c03b223db4b0fa98aa1c0e16ca3ec
Source dataset
uspto-grants-1992_07
Patent number
US05130335

Reaction notes

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