Water → Bis(2-hydroxyphenyl)methane

HRID 1579146Notes

Reaction equation

HRID 1579146 reaction equation
[C:1]1([O:7]C(Cl)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.[OH2:14].[OH-].[Na+].C(N([CH2:22][CH3:23])CC)C>>[CH:2]1[CH:3]=[C:22]([CH2:23][C:2]2[C:1]([OH:7])=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:5]([OH:14])=[CH:6][CH:1]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 15891Phenyl chloroformate

Product 1

HCID 75575Bis(2-hydroxyphenyl)methane

Procedure

62.6 G of chloroformic acid phenyl ester are added dropwise over the course of 30 minutes to a two-phase solution of 40 g of bis-(4-hydroxyphenyl)-methane(bisphenol-F), 600 g of methylene chloride, 300 g of water, 41.4 g of 45% strength sodium hydroxide solution and 0.240 g of triethylamine at 25°C. After stirring for 1 hour, 3.1 g of unreacted bisphenol-F are again isolated from the aqueous phase and the organic phase is washed with dilute sodium hydroxide solution, then with dilute hydrochloric acid and finally with water. After drying the solution and distilling off the methylene chloride, recrystallization of the residue from 300 ml of cyclohexane yields 73.8 g (84% of theory) of bisphenol-F-bisphenyl-carbonate of melting point 97.5 to 98°C.

Sources & evidence

ORD record
ord-5d8b3cb68138473aa94e7beb53581cd7
Source dataset
uspto-grants-1976_01
Patent number
US03931108

Reaction notes

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