HCID 18951516, compound → HCID 18951549, compound

HRID 1492861Notes

Reaction equation

HRID 1492861 reaction equation
C1(C[O:8][C:9]2[C:14]([O:15]CC3C=CC=CC=3)=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:31]=[C:32]([CH:36]=[C:37]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH:38]=2)[C:33]([OH:35])=[O:34])C=CC=CC=1.[H][H]>[Pd].C1COCC1>[OH:8][C:9]1[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH:38]=1)[C:33]([OH:35])=[O:34]

Participants

5

Reactant 2

HCID 18951516HCID 18951516, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18951549HCID 18951549, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.66 g of 3-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]-5-(tetradecyloxy)benzoic acid and 0.3 g of 10% palladium on carbon in 75 ml of THF was stirred in a hydrogen atmosphere until uptake ceased after 4 hours. The usual workup followed by trituration with hexane and filtration gave 1.14 g (91% yield, mp 92°-94°) of 3-[[6-(2,3-dihydroxyphenyl)hexyl]oxy]-5-(tetradecyloxy) benzoic acid.

Workup

  1. filtrationThe usual workup followed by trituration with hexane and filtration

Sources & evidence

ORD record
ord-6768f69f987649f6b031e47df84a2527
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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