Thionyl Chloride → Ethyl alpha,3-dichloro-4-cyclohexylphenylacetate

HRID 436315Notes

Reaction equation

HRID 436315 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14](O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.S(Cl)([Cl:23])=O>>[Cl:23][CH: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:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 21454168HCID 21454168, compound

Product 1

HCID 21454144Ethyl alpha,3-dichloro-4-cyclohexylphenylacetate

Procedure

A mixture of 221.75 g. (0.747 mole) of ethyl 3-chloro-4-cyclohexylphenylglycolate prepared as described in U.S. Pat. No. 3,852,323 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,3-dichloro-4-cyclohexylphenylacetate.

Workup

  1. additionA mixture of 221.75 g
  2. temperatureheated
  3. temperatureto reflux for 6 hours
  4. customThe cold reaction mixture
  5. additionis poured into 1125 ml
  6. stirringof ice-cold water with stirring
  7. extractionThe mixture is extracted with 800 ml
  8. washThe ethereal solution is washed with 450 ml
  9. washby washing twice
  10. dry with materialThe ethereal solution is dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-e63931b187da4e02b006b6a076c7fa02
Source dataset
uspto-grants-1977_02
Patent number
US04008269

Reaction notes

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