Hydrochloric Acid → 1,4-Bis(3-hydroxy-2,2-dimethylpropyl)benzene

HRID 2419855Notes

Reaction equation

HRID 2419855 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]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 213125761,4-Bis(2-carbomethoxy-2-methylpropyl)benzene

Product 1

HCID 205107401,4-Bis(3-hydroxy-2,2-dimethylpropyl)benzeneYield 40.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

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

  1. stirringwas stirred
  2. filtrationfiltered
  3. customSolvent was evaporated from the filtrate
  4. customthe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-05d0a2c327754151afa391e4d70836a3
Source dataset
uspto-grants-1978_08
Patent number
US04107444

Reaction notes

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