Thionyl Chloride → HCID 12849064, compound

HRID 2166538Notes

Reaction equation

HRID 2166538 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:13](O)[C:14]#[N:15])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl>[Cl:19][CH:13]([C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH3:12])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[C:14]#[N:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15583501HCID 15583501, compound

Product 1

HCID 12849064HCID 12849064, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 60 ml of chloroform is dissolved 4.4 g of α-(3,4-diethoxyphenyl)-α-hydroxyacetonitrile and after addition of 1.5 ml of thionyl chloride, the mixture is heated under reflux for 15 minutes. After cooling, the reaction mixture is washed with a saturated aqueous solution of sodium hydrogen carbonate and water in the order mentioned, followed by drying over MgSO4. The solvent is then distilled off to give 4.8 g of a crude oil of α-chloro-α-(3,4-diethoxyphenyl)acetonitrile (quantitative yield). [If desired, this crude oil as it is can be used in the next reaction step.] The above crude oil is then purified by column chromatography (eluent: ether-n-hexane=1:5) and the resulting crystals are recrystallized from n-hexane. Colorless needles, m.p. 61°-62° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 15 minutes
  3. temperatureAfter cooling
  4. washthe reaction mixture is washed with a saturated aqueous solution of sodium hydrogen carbonate and water in the order
  5. dry with materialby drying over MgSO4
  6. distillationThe solvent is then distilled off

Sources & evidence

ORD record
ord-cee45f49711c40aea550b6127c6b00a2
Source dataset
uspto-grants-1983_06
Patent number
US04387101

Reaction notes

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