Hydrochloric Acid → HCID 67944900, compound
Reaction equation
[OH:1][C:2]1[CH:24]=[CH:23][C:5]([CH:6]=[C:7]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14]([CH3:19])([CH3:18])[C:13](=[O:20])[C:12]3([CH3:22])[CH3:21])[CH3:8])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[C:7]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14]([CH3:18])([CH3:19])[CH:13]([OH:20])[C:12]3([CH3:22])[CH3:21])[CH3:8])=[CH:23][CH:24]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1 g of 5-(p-hydroxy-α-methylstyryl)-1,1,3,3-tetramethyl-2-indanone in 10 ml of tetrahydrofuran is added dropwise while cooling with ice to a suspension of 100 mg of lithium aluminium hydride in 5 ml of tetrahydrofuran and the mixture is subsequently left to stir at room temperature for 2 hours. After the dropwise addition of 50 ml of 2N hydrochloric acid at 0° the mixture is extracted with ethyl acetate and the organic phase is washed with water, dried and evaporated. After filtration of the crude product over silica gel (elution agent hexane/ethyl acetate=1:1) it is recrystallized from ethyl acetate/hexane and there are obtained 500 mg of 5-(p-hydroxy-α-methylstyryl)-1,1,3,3-tetramethyl-2-indanol in colourless crystals, m.p. 148°-149°.
Workup
- waitthe mixture is subsequently left
- extractionis extracted with ethyl acetate
- washthe organic phase is washed with water
- customdried
- customevaporated
- filtrationAfter filtration of the crude product over silica gel (elution agent hexane/ethyl acetate=1:1) it
- customis recrystallized from ethyl acetate/hexane and there
Sources & evidence
- ORD record
- ord-3a36e9bead93439c80ae7d56cef7d8ab
- Source dataset
- uspto-grants-1989_09
- Patent number
- US04870219
Reaction notes
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