HCID 14986301, compound → HCID 14986309, compound

HRID 1494221Notes

Reaction equation

HRID 1494221 reaction equation
C1(C[O:8][C:9](=[O:40])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[C:25]([O:32][CH3:33])[C:24]=3[O:34][CH3:35])=[C:12]([CH2:36][CH2:37][CH3:38])[C:11]=2[OH:39])C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[OH:39][C:11]1[C:12]([CH2:36][CH2:37][CH3:38])=[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[C:25]([O:32][CH3:33])[C:24]=2[O:34][CH3:35])[CH:14]=[CH:15][C:10]=1[C:9]([OH:40])=[O:8]

Participants

5

Reactant 2

HCID 14986301HCID 14986301, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14986309HCID 14986309, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6.96 g of 2-hydroxy-4-[6-[2,3-dimethoxy-4-(1-methylethyl)phenyl]hexyloxy]-3-propylbenzoic acid phenylmethyl ester in 150 mL of ethyl acetate and 1.4 g of 10% palladium on carbon was stirred in a hydrogen atmosphere for 3 hours. The reaction mixture was filtered through a Celite pad and the filtrate was concentrated under reduced pressure to 5.45 g, mp 106°-108°, of 2-hydroxy-4-[6-[2,3-dimethoxy-4-(1-methylethyl)phenyl]hexyloxy]-3-propylbenzoic acid.

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. concentrationthe filtrate was concentrated under reduced pressure to 5.45 g, mp 106°-108°, of 2-hydroxy-4-[6-[2,3-dimethoxy-4-(1-methylethyl)phenyl]hexyloxy]-3-propylbenzoic acid

Sources & evidence

ORD record
ord-9b418e130ee04854aba4af7e64c914fe
Source dataset
uspto-grants-1991_06
Patent number
US05025036

Reaction notes

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