Bisphenol A → HCID 86746199, compound

HRID 466244Notes

Reaction equation

HRID 466244 reaction equation
[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)[C:2]#[CH:3].[OH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)([CH3:23])[CH3:22])=[CH:17][CH:16]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:14])=[O:10])=[CH:7][CH:6]=1)[C:2]#[CH:3].[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:14])=[O:10])=[CH:7][CH:6]=1)[C:2]#[CH:3].[OH:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([C:24]2[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=2)([CH3:23])[CH3:22])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6623Bisphenol AHCID 8471TriethylamineHCID 134870934-[(Prop-2-yn-1-yl)oxy]benzoyl chloride

Product 1

HCID 86746199HCID 86746199, compoundYield 271.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 4-propargyloxybenzoyl chloride (17.86 grams, 0.092 moles) in 110 milliliters chloroform is added at room temperature over a 2 hour period to a solution of bisphenol A (9.13 grams, 0.040 moles) and triethylamine (15.0 milliliters, 0.018 moles) in 75 milliliters chloroform. After an additional 1.5 hours, the solution is washed with 5 percent aqueous sodium bicarbonate, then with 1N hydrochloric acid. The organic solution is dried and the solvent is removed by evaporation. The product is purified by recrystallization from a 1:1 solution of toluene in heptane. About 21 grams of product are obtained, reflecting a yield of about 96 percent. Nuclear magnetic resonance spectra confirm the identity of the product, and establish its purity. A dynamic scanning calorimetry run shows a melt endotherm at about 144° C. and a polymerization exotherm with a maximum at about 296° C. The heat of polymerization is about 713 joules/gram.

Workup

  1. washthe solution is washed with 5 percent aqueous sodium bicarbonate
  2. customThe organic solution is dried
  3. customthe solvent is removed by evaporation
  4. customThe product is purified by recrystallization from a 1:1 solution of toluene in heptane

Sources & evidence

ORD record
ord-2dafa8ab912b41678e2876d24f7a4bef
Source dataset
uspto-grants-1992_10
Patent number
US05155196

Reaction notes

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