Acetyl chloride → HCID 131718952, compound

HRID 1653622Notes

Reaction equation

HRID 1653622 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[C:6]([Br:9])[C:5]([Br:10])=[C:4]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)([CH3:13])[CH3:12])[C:3]=1[Br:21].[C:22](Cl)(=[O:24])[CH3:23]>N1C=CC=CC=1>[C:17]([OH:20])(=[O:24])[CH3:18].[C:22]([OH:24])(=[O:8])[CH3:23].[Br:1][C:2]1[C:7]([OH:8])=[C:6]([Br:9])[C:5]([Br:10])=[C:4]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)([CH3:13])[CH3:12])[C:3]=1[Br:21]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 542409822,3,5,6-Tetrabromo-4-[2-(4-hydroxyphenyl)propan-2-yl]phenol

Product 1

HCID 131718952HCID 131718952, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

27.2 g of tetrabromobisphenol A are dissolved in 176.6 ml of pyridine. 7.8 g of acetyl chloride are added slowly to this solution with cooling, and the reaction mixture thus obtained is kept at room temperature overnight. The mixture is filtered, poured into ice water and acidified using concentrated HCl. The precipitated ester is filtered off under suction, taken up in methylene chloride, washed with sodium bicarbonate solution and water, dried and evaporated. The product is recrystallized from acetonitrile, m.p.: 169° C., NMR: 7.42 ppm, 2.40 ppm, 1.68 ppm.

Workup

  1. temperaturewith cooling
  2. customthe reaction mixture thus obtained
  3. filtrationThe mixture is filtered
  4. additionpoured into ice water
  5. filtrationThe precipitated ester is filtered off under suction
  6. washwashed with sodium bicarbonate solution and water
  7. customdried
  8. customevaporated
  9. customThe product is recrystallized from acetonitrile, m.p.: 169° C., NMR: 7.42 ppm, 2.40 ppm, 1.68 ppm

Sources & evidence

ORD record
ord-760435b252b644cca02339ea725cad5f
Source dataset
uspto-grants-1995_04
Patent number
US05403697

Reaction notes

Loading…