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

HRID 660836Notes

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.[CH2:18](Br)[CH:19]=[CH2:20].C(=O)([O-])[O-].[K+].[K+].[CH3:28][C:29]([CH3:31])=O>>[CH2:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:31][CH:29]=[CH2:28])=[CH:15][CH:16]=2)([CH3:10])[CH3:9])=[CH:6][CH:7]=1)[CH:19]=[CH2:20]

Participants

Reactant 4

HCID 180Acetone

HCID 6623Bisphenol A

HCID 7841Allyl bromide

HCID 11430Potassium Carbonate

Product 1

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

Conditions

Temperature: 50 °C

Procedure

A mixture of bisphenol A (Sigma-Aldrich) (16.78 g, 74 mmol), allyl bromide (Sigma-Aldrich) (24.00 g, 200 mmol), potassium carbonate (Sigma-Aldrich) (30.00 g, 217 mmol), eighteen-crown-six (Sigma-Aldrich) (0.10 g), and acetone (250 ml) was mechanically stirred at 50° C. for 17 hours. The mixture was then filtered, and the filtrate concentrated under vacuum. The residue was purified by column chromatography over silica gel (10 wt % ethyl acetate in hexane) to yield bisphenol A diallyl ether as a colorless oil (20.00 g).

Workup

filtrationThe mixture was then filtered
concentrationthe filtrate concentrated under vacuum
customThe residue was purified by column chromatography over silica gel (10 wt % ethyl acetate in hexane)

Sources & evidence

ORD record: ord-b3cba527ae6e4a36b9b6113e59ff65e1
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084515B2

Reaction notes

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