Hydrochloric Acid → (S)-3-(2-hydroxyethyl)-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH2:10][C@H:11]1[C:20]([CH3:22])([CH3:21])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[CH:18]=2)[C:13]([CH3:25])([CH3:24])[CH2:12]1)(O)=[O:8].Cl>O1CCCC1>[OH:8][CH2:7][CH2:10][C@H:11]1[C:20]([CH3:21])([CH3:22])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[CH:18]=2)[C:13]([CH3:25])([CH3:24])[CH2:12]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A suspension of lithium aluminum hydride (16.8 g; 0.442 mol) in tetrahydrofuran (200 ml) was heated up to 60° C., a solution of (S)-3-carboxymethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronapthalene ([α]546 +25.3° (C=1 in benzene)) (76.4 g; 0.294 mol) in tetrahydrofuran was added dropwise thereto. The resultant mixture was stirred at 60° C. for 2 hours. The reaction mixture was cooled, treated with dilute hydrochloric acid and extracted with toluene (200 ml). The extract was washed with dilute hydrochloric acid, saturated sodium carbonate solution and saturated sodium chloride solution in order, dried over anhydrous sodium sulfate and concentrated to give (S)-3-(2-hydroxyethyl)-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (70.5 g; 0.28 mol; 97.5%). [α]546 -8.1° (C=0.62 in ethanol).
Workup
- temperatureThe reaction mixture was cooled
- extractionextracted with toluene (200 ml)
- washThe extract was washed with dilute hydrochloric acid, saturated sodium carbonate solution and saturated sodium chloride solution in order
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-945723e99cc348399505be19fe20a94b
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04767882
Reaction notes
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