M-Cresol → 3-(2,2,2-Trichloro-1-acetoxy-ethoxy)-toluene

HRID 372468Notes

Reaction equation

HRID 372468 reaction equation
[O:1]=[CH:2][C:3]([Cl:6])([Cl:5])[Cl:4].[CH:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:14].C(N(CC)CC)C.[C:22](Cl)(=[O:24])[CH3:23]>CCOCC>[C:22]([O:1][CH:2]([O:13][C:12]1[CH:7]=[C:8]([CH3:14])[CH:9]=[CH:10][CH:11]=1)[C:3]([Cl:6])([Cl:5])[Cl:4])(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 342M-CresolHCID 6367Acetyl chlorideHCID 6407ChloralHCID 8471Triethylamine

Product 1

HCID 205689273-(2,2,2-Trichloro-1-acetoxy-ethoxy)-toluene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of anhydrous chloral (37.0 g) in dry ether (125 ml) was added meta-cresol (27.0 g) and the mixture was stirred at the ambient temperature for 20 minutes, after which it was cooled to 10° C and a solution of triethylamine (25.25 g) in dry ether (100 ml) was slowly added. Acetyl chloride (20.0 g) was then carefully added to the stirred mixture and stirring was continued for 1 hour. The insoluble material was removed by filtration and the filtrate dried over anhydrous magnesium sulphate. After removal of the ether by evaporation under reduced pressure the residual oil was distilled under high vacuum and the fraction boiling at 132°-135°/0.5 mm Hg collected. Infra-red and nuclear magnetic spectroscopic analysis indicated that this was 1(3-tolyloxy)-2,2,2-trichloroethyl acetate.

Workup

  1. temperatureafter which it was cooled to 10° C
  2. stirringstirring
  3. waitwas continued for 1 hour
  4. customThe insoluble material was removed by filtration
  5. dry with materialthe filtrate dried over anhydrous magnesium sulphate
  6. customAfter removal of the ether
  7. customby evaporation under reduced pressure the residual oil
  8. distillationwas distilled under high vacuum
  9. customthe fraction boiling at 132°-135°/0.5 mm Hg collected

Sources & evidence

ORD record
ord-844676e9cf5f49fe810fe7e4175fc1a3
Source dataset
uspto-grants-1978_05
Patent number
US04091110

Reaction notes

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