Benzyl Alcohol → Benzyl 2,2,2-trichloroacetimidate

HRID 1699741Notes

Reaction equation

HRID 1699741 reaction equation
[OH-].[Na+].CCOCC.[CH2:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl:16][C:17]([Cl:21])([Cl:20])[C:18]#[N:19]>CO.CCCCCC>[Cl:16][C:17]([Cl:21])([Cl:20])[C:18]([O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[NH:19]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 3283Diethyl EtherHCID 11011TrichloroacetonitrileHCID 14798Sodium Hydroxide

Product 1

HCID 144968Benzyl 2,2,2-trichloroacetimidateYield 88%

Reagents, catalysts & solvents 1

HCID 21896459Hexane methanolSolvent

Procedure

0.868 g of 60% sodium hydroxide was measured and placed in a 100 ml flask with a two-way cock, and the gas in the flask was replaced with nitrogen. The sodium hydroxide was twice washed with hexane, and then dried under reduced pressure. The gas in the flask was again replaced with nitrogen, and 20 ml of diethyl ether was then added to form a suspension. The flask was immersed in an ice water bath, and the suspension was stirred for about five minutes. 20 ml of an ether solution containing 7.19 g of benzyl alcohol was added by the use of a cannula, and the reaction solution was stirred at such a temperature for 20 minutes, mixed with 10 ml of trichloroacetonitrile dropwisely added thereto, and stirred for 2 hours, while the temperature of the solution was gradually raised up to room temperature. After the reaction was finished, the reaction solution was mixed with a methanol/hexane solution, and further stirred for 3 hours. The insolubles were filtered off. The filtrate was concentrated under reduced pressure, and then again mixed with hexane. The impurities were filtered off. The solvent was distilled away from the filtrate under reduced pressure to obtain the title compound as a yellow oil (14.84 g, 88%).

Workup

  1. customplaced in a 100 ml flask with a two-way cock
  2. washThe sodium hydroxide was twice washed with hexane
  3. customdried under reduced pressure
  4. additionwas then added
  5. customto form a suspension
  6. customThe flask was immersed in an ice water bath
  7. additionwas added by the use of a cannula
  8. stirringthe reaction solution was stirred at such a temperature for 20 minutes
  9. additiondropwisely added
  10. stirringstirred for 2 hours, while the temperature of the solution
  11. stirringfurther stirred for 3 hours
  12. filtrationThe insolubles were filtered off
  13. concentrationThe filtrate was concentrated under reduced pressure
  14. additionagain mixed with hexane
  15. filtrationThe impurities were filtered off
  16. distillationThe solvent was distilled away from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-aee84d50276a4774940619e8ce492627
Source dataset
uspto-grants-2002_02
Patent number
US06348478B1

Reaction notes

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