Hexane → 3-[[6-(2,3-Dihydroxyphenyl) hexyl]oxy]-5-(octadecyloxy)benzoic acid

HRID 1492840Notes

Reaction equation

HRID 1492840 reaction equation
C1(C[O:8][C:9](=[O:64])[C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=[C:12]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([O:48]CC4C=CC=CC=4)[C:43]=3[O:56]CC3C=CC=CC=3)[CH:11]=2)C=CC=CC=1.[H][H].CCCCCC>[Pd].C1COCC1>[OH:56][C:43]1[C:44]([OH:48])=[CH:45][CH:46]=[CH:47][C:42]=1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][O:35][C:12]1[CH:11]=[C:10]([CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=1)[C:9]([OH:64])=[O:8]

Participants

6

Reactant 3

HCID 8058HexaneHCID 15233477HCID 15233477, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 98516283-[[6-(2,3-Dihydroxyphenyl) hexyl]oxy]-5-(octadecyloxy)benzoic acidYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.0 g of 3-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]-5-(octadecyloxy)benzoic acid phenylmethyl ester and 0.5 g of 10% palladium on carbon in 100 ml of THF was stirred in a hydrogen atmosphere until uptake ceased after 5 hours. The usual workup followed by trituration of the crude product with hexane gave 1.2 g (88% yield, mp 92°-94°) of 3-[[6-(2,3-dihydroxyphenyl) hexyl]oxy]-5-(octadecyloxy)benzoic acid.

Sources & evidence

ORD record
ord-6596376abaa74586b267c53086a3b0e3
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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