3-(Octadecyloxy)-5-(3-phenoxypropoxy)benzoic acid phenylmethyl ester → 3-(Octadecyloxy)-5-(3-phenoxypropoxy)benzoic acid

HRID 488258Notes

Reaction equation

HRID 488258 reaction equation
C1(C[O:8][C:9](=[O:46])[C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:13]=[C:12]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH:11]=2)C=CC=CC=1.[H][H]>[Pd].C1COCC1.C(OCC)(=O)C>[CH2:28]([O:27][C:12]1[CH:11]=[C:10]([CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:13]=1)[C:9]([OH:46])=[O:8])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]

Participants

6

Reactant 2

HCID 152328333-(Octadecyloxy)-5-(3-phenoxypropoxy)benzoic acid phenylmethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 152328343-(Octadecyloxy)-5-(3-phenoxypropoxy)benzoic acidYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 14.6 g of 3-(octadecyloxy)-5-(3-phenoxypropoxy) benzoic acid phenylmethyl ester and 3 g of 10% palladium on carbon in 200 ml THF and 20 ml ethyl acetate was shaken in a hydrogen atmosphere at room temperature for 2 hours. The catalyst was removed by filtration and the filtrate was concentrated to a solid which was recrystallized from ether-hexane to give 11.8 g (95% yield, mp 79°-81°) of 3-(octadecyloxy) -5-(3-phenoxypropoxy)benzoic acid.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to a solid which
  3. customwas recrystallized from ether-hexane

Sources & evidence

ORD record
ord-96f09601eed14b409cc04c9564e81934
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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