Pyridine → alpha-Chloro-alpha-(2,4-dichlorophenyl)-acetic acid t-butyl ester

HRID 848749Notes

Reaction equation

HRID 848749 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[Cl:12][CH:13]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])[C:14](Cl)=[O:15]>ClCCl>[C:1]([O:5][C:14](=[O:15])[CH:13]([Cl:12])[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6386tert-ButanolHCID 20564372alpha-Chloro-alpha-(2,4-dichlorophenyl)-acetyl chloride

Product 1

HCID 54191230alpha-Chloro-alpha-(2,4-dichlorophenyl)-acetic acid t-butyl esterYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

While stirring and with ice cooling, a solution of 17.6 g of t-butanol and 19.2 ml of pyridine in 60 ml of dichloromethane is dripped into a solution, cooled at 5° C., of 62 g of α-chloro-α-(2,4-dichlorophenyl)-acetyl chloride in 60 ml of dichloromethane in such a manner that the temperature of the reaction mixture stays below 10° C. After all the solution has been dripped in, the mixture is stirred overnight at room temperature, is then diluted with 100 ml of dichloromethane and extracted 5 times, each time with 100 ml of water. The organic phase is dried over magnesium sulfate and distilled after the solvent has been evaporated. There is obtained 58 g of α-chloro-α-(2,4-dichlorophenyl)-acetic acid t-butyl ester as a colorless oil; b.p. 98°-103° C./0.13 mbar.

Workup

  1. customstays below 10° C
  2. stirringis stirred overnight at room temperature
  3. extractionextracted 5 times
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. distillationdistilled after the solvent
  6. customhas been evaporated

Sources & evidence

ORD record
ord-f400aa52fe434e649fda6c635634b4cc
Source dataset
uspto-grants-1981_10
Patent number
US04297364

Reaction notes

Loading…