1-Propanol → Benzene, 1,1'-(1-methylethylidene)bis[4-(2-propen-1-yloxy)-

HRID 866528Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:20](Cl)[CH:21]=[CH2:22].[CH2:24](O)[CH2:25][CH3:26]>>[CH3:9][C:8]([C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:26][CH:25]=[CH2:24])=[CH:15][CH:16]=1)([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:20][CH:21]=[CH2:22])=[CH:7][CH:6]=1)[CH3:10]

Participants

Reactant 4

HCID 10311-Propanol

HCID 6623Bisphenol A

HCID 7850Allyl chloride

HCID 14798Sodium Hydroxide

Product 1

HCID 77333Benzene, 1,1'-(1-methylethylidene)bis[4-(2-propen-1-yloxy)-

Procedure

Bisphenol A (228 g), NaOH (82.5 g) and n-propanol (1 liter) are heated under reflux. After everything has gone into solution, 200 ml of allyl chloride are added slowly. After three hours, the mixture is virtually neutral. It is stirred for a further three hours, whilst boiling under reflux. After cooling to room temperature, the NaCl which has precipitated is filtered off and the n-propanol is distilled off. The crude diallyl ether of bisphenol A (308 g) which is thus obtained is taken up in methylene chloride and washed with water. After separating off the aqueous phase, the methylene chloride is distilled off again. The resulting pure diallyl ether of bisphenol A is dried over sodium sulphate.

Workup

temperatureunder reflux
additionare added slowly
temperatureunder reflux
customthe NaCl which has precipitated
filtrationis filtered off
distillationthe n-propanol is distilled off

Sources & evidence

ORD record: ord-deede02d003048f4a7fe88271740302c
Source dataset: uspto-grants-1978_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04100140

Reaction notes

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