Lithium Hydroxide → 3-allyl-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2H-1-benzofuran-6-carboxylic acid
Reaction equation
[CH2:1]([C:4]1([C:17]2[CH:26]=[CH:25][C:24]3[C:23]([CH3:28])([CH3:27])[CH2:22][CH2:21][C:20]([CH3:30])([CH3:29])[C:19]=3[CH:18]=2)[C:8]2[CH:9]=[CH:10][C:11]([C:13]([O:15]C)=[O:14])=[CH:12][C:7]=2[O:6][CH2:5]1)[CH:2]=[CH2:3].[OH-].[Na+].[OH-].[Li+]>>[CH2:1]([C:4]1([C:17]2[CH:26]=[CH:25][C:24]3[C:23]([CH3:28])([CH3:27])[CH2:22][CH2:21][C:20]([CH3:30])([CH3:29])[C:19]=3[CH:18]=2)[C:8]2[CH:9]=[CH:10][C:11]([C:13]([OH:15])=[O:14])=[CH:12][C:7]=2[O:6][CH2:5]1)[CH:2]=[CH2:3]Participants
4
Procedure
A mixture of methyl 3-allyl-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2H-1-benzofuran-6-carboxylate (240 mg, 0.61 mmol), sodium hydroxide (0.12 g, 3 mmol) and lithium hydroxide (0.06 g, 3 mmol) is stirred at room temperature for 3 days. The mixture is concentrated on a rotary evaporator under vacuum at 40° C. 10 ml of water and 10 ml of ethyl acetate are added. The mixture is acidified with concentrated hydrochloric acid solution to pH 1. After separation of the phases by settling, the organic phase is washed twice with 10 ml of water, dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. The product is obtained by recrystallization from a heptane/ethyl ether mixture (3/1).
Workup
- concentrationThe mixture is concentrated on a rotary evaporator under vacuum at 40° C
- addition10 ml of water and 10 ml of ethyl acetate are added
- customAfter separation of the phases
- washthe organic phase is washed twice with 10 ml of water
- dry with materialdried over magnesium sulphate
- concentrationconcentrated on a rotary evaporator under vacuum at 40° C
- customThe product is obtained by recrystallization from a heptane/ethyl ether mixture (3/1)
Sources & evidence
- ORD record
- ord-cc78f16b09ab4ba4a766380b55ec671e
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05981776
Reaction notes
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