Bisphenol A → HCID 85771059, compound

HRID 1381039Notes

Reaction equation

O[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])C)=[CH:4][CH:3]=1.C(=O)([O:21][CH2:22][CH:23]1[CH2:27]OC(=O)[O:24]1)OC.[F-].[K+].[CH2:32](OCCO)CCC.[Al]>>[CH3:32][C:4]([CH3:3])=[C:5]1[CH:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:27][CH:23]([OH:24])[CH2:22][OH:21])=[CH:15][CH:16]=2)[CH:10]=[CH:2][CH:7]=[CH:6]1

Participants

Reactant 5

HCID 6623Bisphenol A

HCID 81332-Butoxyethanol

HCID 522689Potassium Fluoride

HCID 5359268Aluminum

HCID 13628763Methyl (2-oxo-1,3-dioxolan-4-yl)methyl carbonate

Product 1

HCID 85771059HCID 85771059, compoundYield 90%

Conditions

Temperature: 170 °C

Procedure

A mixture of 5.58 g (0.03 mole) of bisphenol A, 5.28 g (0.03 mole) of methyl 2-oxo-1,3-dioxolan-4-ylmethyl carbonate, 0.174 g (0.003 mole) of KF, and 5 ml of 2-(n-butoxy)ethanol is placed in a 50-ml resin pot equipped with a mechanical stirrer and a distillation head and warmed with stirring to 170° C. After heating at 170° C. for 4 hours, the gas evolution appeared to cease and the reaction mixture becomes viscous. The hot reaction mixture is poured into 8 aluminum cups and the solvent is evaporated in a vacuum oven (150° C.) for 24 hours to give 6.8 g (90 percent yield) of a yellow, brittle polymer with 12,000 molecular weight and m.p.=116° C. "p" can be calculated to be about 40. The above structure of the polymer is confirmed by nuclear magnetic resonance spectra data.

Workup

custompot equipped with a mechanical stirrer
temperaturea distillation head and warmed
temperatureAfter heating at 170° C. for 4 hours
customthe solvent is evaporated in a vacuum oven (150° C.) for 24 hours
customto give 6.8 g (90 percent yield) of a yellow, brittle polymer with 12,000 molecular weight and m.p.=116° C. "p"

Sources & evidence

ORD record: ord-6dd6237ceb3c47d9aec5fc389c4ae542
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04584408

Reaction notes

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