Benzyl 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]-benzoate → 4-[3-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propanoyloxy]benzoic acid
Reaction equation
[CH3:1][C:2]1([CH3:35])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH:14]=[CH:15][C:16]([O:18][C:19]3[CH:34]=[CH:33][C:22]([C:23]([O:25]CC4C=CC=CC=4)=[O:24])=[CH:21][CH:20]=3)=[O:17])[CH:5]=[CH:4][C:3]1=2>[Pd].O1CCOCC1>[CH3:1][C:2]1([CH3:35])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH2:14][CH2:15][C:16]([O:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:33][CH:34]=3)=[O:17])[CH:5]=[CH:4][C:3]1=2Participants
4
Procedure
1.7 g (3.7 mmol) of benzyl 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]-benzoate, 40 ml of dioxane and 340 mg of palladium on charcoal (10%) are introduced into a reactor. The mixture is hydrogenated at 40° C. and at a pressure of 7 bar for three hours. The catalyst is filtered off and the mixture is evaporated to dryness. The solid obtained is triturated from hexane, filtered off and dried. 1.2 g (85%) of 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propanoyloxy]benzoic acid, with a melting point of 183-4° C., are collected.
Workup
- filtrationThe catalyst is filtered off
- customthe mixture is evaporated to dryness
- customThe solid obtained
- customis triturated from hexane
- filtrationfiltered off
- customdried
- custom1.2 g (85%) of 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propanoyloxy]benzoic acid, with a melting point of 183-4° C., are collected
Sources & evidence
- ORD record
- ord-bf7797ef9e2248f3b769adb2b91aeb75
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06326510B1
Reaction notes
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