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

HRID 462028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 462028
[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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 213125864,4'-Bis(3-hydroxy-2,2-dimethylpropyl)biphenylAusbeute 58,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-98ffd99c2fae401c88ea59df8f3e4273
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04065431

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