4-[2-(4,4-Dimethyl-chroman-7-yl)-heptanoyloxy]-benzoic acid benzyl ester → 4-[2-(4,4-Dimethyl-chroman-7-yl)-heptanoyloxy]-benzoic acid

HRID 899297Notes

Reaction equation

HRID 899297 reaction equation
C([O:8][C:9](=[O:37])[C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17](=[O:36])[CH:18]([C:24]2[CH:33]=[C:32]3[C:27]([C:28]([CH3:35])([CH3:34])[CH2:29][CH2:30][O:31]3)=[CH:26][CH:25]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][CH:11]=1)C1C=CC=CC=1>C([O-])(=O)C.[Pd]>[CH3:34][C:28]1([CH3:35])[C:27]2[C:32](=[CH:33][C:24]([CH:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:17]([O:16][C:13]3[CH:12]=[CH:11][C:10]([C:9]([OH:37])=[O:8])=[CH:15][CH:14]=3)=[O:36])=[CH:25][CH:26]=2)[O:31][CH2:30][CH2:29]1

Participants

4

Reactant 1

HCID 692169914-[2-(4,4-Dimethyl-chroman-7-yl)-heptanoyloxy]-benzoic acid benzyl ester

Product 1

HCID 101362674-[2-(4,4-Dimethyl-chroman-7-yl)-heptanoyloxy]-benzoic acidYield 60.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 175AcetateSolvent

Procedure

A solution of 4-[2-(4,4-dimethyl-chroman-7-yl)-heptanoyloxy]-benzoic acid benzyl ester (152 mg, 0.3 mmol) in 10 mL of elthyl acetate with 32 mg of 10% palladium on carbon, was subjected to 1 atm. H2. After 2 h, the mixture was filtered through Celite and silica gel, concentrated under vacumn and purified by flash chromatography (gradient elution, 10-50% ethyl acetate/hexane) to afford 74 mg (59%) of 4-[2-(4,4-dimethyl-chroman-7-yl)-heptanoyloxy]-benzoic acid.

Workup

  1. filtrationthe mixture was filtered through Celite and silica gel
  2. concentrationconcentrated under vacumn
  3. custompurified by flash chromatography (gradient elution, 10-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a0f6b6de2389412cb6d70b3513ae3a67
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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