Triethylamine → Bisphenol A

HRID 1834084Notes

Reaction equation

HRID 1834084 reaction equation
CC(C(Cl)=O)=C.OCC[O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26]CCO)=[CH:22][CH:21]=2)([CH3:19])[CH3:18])=[CH:13][CH:12]=1.C(N(CC)CC)C>CC(C)=O>[OH:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([C:20]2[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=2)([CH3:19])[CH3:18])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 61909Bisphenol A bis(2-hydroxyethyl)ether

Product 1

HCID 6623Bisphenol A

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

45 g. of methacryl chloride is slowly added to a mixture of 66.2 g. of 2,2-bis[4-(2-hydroxyethoxy)phenyl]-propane, 41 g. of triethylamine and 300 ml. of dry acetone. The temperature is maintained below 32° C with cooling. The resulting amine hydrochloride is filtered off and washed with acetone. The acetone solution is added to 500 ml. of ice and water, the oily layer recovered and washed with sodium bicarbonate, followed by water, and dried at 40° C. in a vacuum with a stream of air passing through the liquid. The infrared spectrum of the product contains only a very small band indicating hydroxyl hydrogens, a large ester carbonyl band, and a carbon double bond band.

Workup

  1. temperatureThe temperature is maintained below 32° C
  2. temperaturewith cooling
  3. filtrationThe resulting amine hydrochloride is filtered off
  4. washwashed with acetone
  5. additionThe acetone solution is added to 500 ml
  6. customof ice and water, the oily layer recovered
  7. washwashed with sodium bicarbonate
  8. customdried at 40° C. in a vacuum with a stream of air passing through the liquid

Sources & evidence

ORD record
ord-679174bb0720438eb26c74797bc25c41
Source dataset
uspto-grants-1978_01
Patent number
US04068082

Reaction notes

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