Pyridine → 1,1-Dimethylethyl dichloroacetate

HRID 1439350Notes

Reaction equation

HRID 1439350 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.CCOCC.[Cl:17][CH:18]([Cl:22])[C:19](Cl)=[O:20]>O>[C:1]([O:5][C:19](=[O:20])[CH:18]([Cl:22])[Cl:17])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 6386tert-ButanolHCID 6593Dichloroacetyl chloride2×

Product 1

HCID 30164831,1-Dimethylethyl dichloroacetateYield 76.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

74 g of t-butylalcohol, 79 g of pyridine and 250 ml of anhydrous ether were heated to boiling and 146 g of dichloroacetyl chloride were added dropwise to the reaction mixture at such a rate that the mixture continued to boil without further supply of heat. When all the dichloroacetyl chloride has been added, boiling was continued for 3 hours. Water was then added to the reaction mixture and the ethereal phase was separated off. The resulting reaction solution was processed in the usual manner to yield 140 g of α, α-dichloroacetic acid-t-butyl ester.

Workup

  1. temperatureof heat
  2. customthe ethereal phase was separated off
  3. customThe resulting reaction solution

Sources & evidence

ORD record
ord-56d6c3ec55664270bdaf773f46a8b755
Source dataset
uspto-grants-1977_11
Patent number
US04059447

Reaction notes

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