Hydrochloric Acid → 4,4'-Bis(3-hydroxy-2,2-dimethylpropyl)biphenyl

HRID 462028Notes

Reaction equation

HRID 462028 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]([CH3:34])([CH3:33])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C:26]([CH3:32])([C:28](OC)=[O:29])[CH3:27])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)(OC)=[O:8].[NH4+].[Cl-].Cl>O1CCCC1.C(OCC)(=O)C>[OH:8][CH2:7][C:11]([CH3:34])([CH3:33])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C:26]([CH3:32])([CH3:27])[CH2:28][OH:29])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 20314658HCID 20314658, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 213125864,4'-Bis(3-hydroxy-2,2-dimethylpropyl)biphenylYield 58.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5.94 g of lithium aluminum hydride in 1500 ml of dry tetrahydrofuran, 30 g of 4,4'-bis(2-carbomethoxy-2-methylpropyl)biphenyl was slowly added. The reaction mixture thickened on stirring overnight. Then there was added 150 ml of ethyl acetate, 60 ml of saturated aqueous NH4Cl and 150 ml of concentrated HCl. After thorough mixing, the solid and liquid were separated by filtration. The filtrate was evaporated to dryness and the residue recrystallized from benzene to obtain 15 g of 4,4'-bis(3-hydroxy-2,2-dimethylpropyl)biphenyl. The solid from the above filtration was slurried with 50 ml of H2O, 10 ml of concentrated HCl and 50 ml of benzene and the mixture was heated at reflux for 1 hr. The benzene layer was separated, dried with MgSO4 at 80° C, filtered hot and then cooled to precipitate an additional 10 g of 4,4'-bis(3-hydroxy-2,2-dimethylpropyl)biphenyl, m.p. 168°-170° C.

Workup

  1. customAfter thorough mixing, the solid and liquid were separated by filtration
  2. customThe filtrate was evaporated to dryness
  3. customthe residue recrystallized from benzene

Sources & evidence

ORD record
ord-98ffd99c2fae401c88ea59df8f3e4273
Source dataset
uspto-grants-1977_12
Patent number
US04065431

Reaction notes

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