Phenol, tribromo- → o-Chloromethylbenzoic acid tribromophenyl ester

HRID 2419171Notes

Reaction equation

HRID 2419171 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Br:9])[C:3]=1[Br:10].[Cl:11][CH2:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16].C1([O-])C=CC=CC=1>[OH-].[Na+].COCCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:15](=[O:16])[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[CH2:12][Cl:11])=[C:4]([Br:9])[C:3]=1[Br:10]

Participants

6

Reactant 3

HCID 32928Phenol, tribromo-HCID 119047PhenolateHCID 30163952-(Chloromethyl)benzoyl chloride

Product 1

HCID 20314963o-Chloromethylbenzoic acid tribromophenyl esterYield 82%

Reagents, catalysts & solvents 2

HCID 80192-MethoxyethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

In a two-liter three-necked flask, 40 g of sodium hydroxide was dissolved in 950 ml of methyl glycol at 60° C, and then 331 g (= 1 mole) of tribromophenol was stirred in, and then 189 g (= 1 mole) of o-chloromethyl benzoyl chloride was added, drop by drop, with stirring, over a period of 13/4 hours, at a reaction mixture temperature not exceeding 40° C, into the clear phenolate solution, cooled to 30° to 40° C. Stirring was then continued for one hour at room temperature; the mixture was then cooled to 0° C, the crystallizate was suction filtered and washed free of sodium chloride with water, and dried at 80° C in a vacuum drying chamber. 397 g (= 82% yield) was obtained of o-chloromethylbenzoic acid tribromophenyl ester melting at 180°-110° C.

Workup

  1. additionwas added
  2. temperaturecooled to 30° to 40° C
  3. filtrationfiltered
  4. washwashed free of sodium chloride with water
  5. customdried at 80° C in a vacuum
  6. customdrying chamber

Sources & evidence

ORD record
ord-e955d7758db243cca2a9fdfc76a2a6f9
Source dataset
uspto-grants-1978_08
Patent number
US04105628

Reaction notes

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