Thionyl Chloride → HCID 21506283, compound

HRID 1287676Notes

Reaction equation

HRID 1287676 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][CH:15](O)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.S(Cl)([Cl:24])=O>>[Cl:24][CH:15]([CH2:14][C:4]1[CH:5]=[CH:6][C:7]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[C:2]([Cl:1])[CH:3]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 21506243HCID 21506243, compound

Product 1

HCID 21506283HCID 21506283, compound

Procedure

A mixture of 232 g. (0.747 mole) of ethyl β-(3-chloro-4-cyclohexylphenyl)lactate is stirred with 106.67 g. (0.895 mole) of thionyl chloride at room temperature for 24 hours and then heated to reflux for 6 hours. The cold reaction mixture is poured into 1125 ml. of ice-cold water with stirring. The mixture is extracted with 800 ml. of ether. The ethereal solution is washed with 450 ml. of cold saturated sodium hydrocarbonate solution followed by washing twice, each time with 250 ml. of cold water. The ethereal solution is dried over anhydrous sodium sulfate and filtered. The solvent is removed in vacuo to obtain ethyl α-chloro-β-(3-chloro-4-cyclohexylphenyl)propionate.

Workup

  1. additionA mixture of 232 g
  2. temperatureheated
  3. temperatureto reflux for 6 hours
  4. customThe cold reaction mixture
  5. additionis poured into 1125 ml
  6. extractionThe mixture is extracted with 800 ml
  7. washThe ethereal solution is washed with 450 ml
  8. washby washing twice
  9. dry with materialThe ethereal solution is dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-cc4270d6e5d14c2dba726167a77eba6c
Source dataset
uspto-grants-1976_10
Patent number
US03985788

Reaction notes

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