Hydrochloric Acid → 1,4-Bis(3-hydroxy-2,2-dimethylpropyl)benzene
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]([CH3:28])([CH3:27])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([CH3:26])([C:22](OC)=[O:23])[CH3:21])=[CH:15][CH:14]=1)(OC)=[O:8].[NH4+].[Cl-].Cl>C(OCC)(=O)C.O1CCCC1>[OH:8][CH2:7][C:11]([CH3:28])([CH3:27])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([CH3:26])([CH3:21])[CH2:22][OH:23])=[CH:15][CH:14]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To 500 ml of dry tetrahydrofuran was added 11.4 g of lithium aluminum hydride and 60 g of 1,4-bis(2-carbomethoxy-2-methylpropyl)benzene. The mixture was stirred overnight at room temperature. To the thick reaction mixture was added 300 ml of ethyl acetate, 30 ml of saturated aqueous NH4Cl and 5 ml of concentrated HCl. The mixture was stirred and filtered. Solvent was evaporated from the filtrate and the residue was recrystallized from benzene to obtain 20 g of 1,4-bis(3-hydroxy-2,2-dimethylpropyl)benzene. The solid from the above filtration was slurried with 50 ml of H2O, 20 ml of concentrated HCl and 150 ml of benzene and heated at reflux for 1 hour. The benzene layer was then separated, dried over MgSO4 at 80° C, filtered hot and then cooled to precipitate an additional 10 g of 1,4-bis(3-hydroxy-2,2-dimethylpropyl)benzene, m.p. 104°-105° C.
Workup
- stirringThe mixture was stirred
- filtrationfiltered
- customSolvent was evaporated from the filtrate
- customthe residue was recrystallized from benzene
Sources & evidence
- ORD record
- ord-d32db01b93a9475eb423ad5ba2a06eb7
- Source dataset
- uspto-grants-1977_12
- Patent number
- US04065431
Reaction notes
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