Water → HCID 14875837, compound

HRID 1761796Notes

Reaction equation

HRID 1761796 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[C:9](=[O:12])[CH2:10][CH3:11].[OH2:13].[C:14]1([CH3:20])C=CC=CC=1>C(C(C)=O)C(C)C>[CH3:11][C:10]([C:4]1[CH:5]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=1)([CH2:14][CH3:20])[C:9]([OH:12])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 996Phenol2×HCID 1140TolueneHCID 6569Methyl Ethyl Ketone2×

Product 1

HCID 14875837HCID 14875837, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A solution of 23.1 g phenol (0.25 moles) and 53.1 g 2-butanone (0.74 moles) is pumped into a CO pressurized reactor containing 10 g water (0.56 moles) and 91 g AHF (4.55 moles). At a starting pressure of 1430 psig and 74°-81° C., the phenol and 2-butanone are charged in (66 minutes pumping time). After complete addition of the reactants, the pressure decreases from 2015 psig to 1700 psig over an additional 188 minutes at the reaction temperature. 8.4 g of (II) is isolated as toluene and methyl isobutyl ketone soluble from an aqueous HF extraction representing 55% phenol conversion and 32% selectivity to (II). Crystallization from toluene and CHCl3 yielded the product (m.p. 129°-131° C.) with structure II verified by nmr.

Workup

  1. additionAfter complete addition of the reactants

Sources & evidence

ORD record
ord-229304b2ce83490eb03a795ae5465e71
Source dataset
uspto-grants-1989_05
Patent number
US04827845

Reaction notes

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