6-(4'-Decyloxybenzoyloxy)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid benzyl ester → 6-(4'-Decyloxybenzoyloxy)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

HRID 1415

Reaction equation

HRID 1415 reaction equation
[H][H].C([O:10][C:11]([C:13]1[CH:22]=[CH:21][C:20]2[CH2:19][CH:18]([O:23][C:24](=[O:42])[C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:27][CH:26]=3)[CH2:17][CH2:16][C:15]=2[CH:14]=1)=[O:12])C1C=CC=CC=1>[Pd].O1CCCC1>[CH2:32]([O:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]([O:23][CH:18]2[CH2:17][CH2:16][C:15]3[CH:14]=[C:13]([C:11]([OH:12])=[O:10])[CH:22]=[CH:21][C:20]=3[CH2:19]2)=[O:42])=[CH:26][CH:27]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

5

Reactant 2

HCID 544399726-(4'-Decyloxybenzoyloxy)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 190700256-(4'-Decyloxybenzoyloxy)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acidYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Hydrogen gas was blown into a mixture of 0.53 g (1.0 mmol) of 6-(4'-decyloxybenzoyloxy)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid benzyl ester, 0.11 g of 5% palladium/carbon and 10 ml of tetrahydrofuran with stirring at room temperature and ordinary pressure for 15 hours. The reaction mixture was filtered using Celite as a filter aid, and the filtrate was concentrated to obtain 0.42 g (0.93 mmol) of 6-(4'-decyloxybenzoyloxy)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ccd7d3bc80234865b14e3c2556c0baf6
Source dataset
uspto-grants-1998_03
Patent number
US05725798

Linked notes

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