Thionyl Chloride → HCID 10564751, compound

HRID 1460456Notes

Reaction equation

HRID 1460456 reaction equation
O[CH:2]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].S(Cl)([Cl:22])=O>>[Cl:22][CH:2]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 14997421HCID 14997421, compound

Product 1

HCID 10564751HCID 10564751, compoundYield 89%

Procedure

To ethyl 2-hydroxy-2-(4-cyclohexylphenyl)acetate (52 g) was added thionyl chloride (100 ml) and the mixture was refluxed for 1 hour. The reaction mixture was then concentrated under reduced pressure, and the residual oil was diluted with water and extracted with ether. The ether layer was washed with water, dried (MgSO4) and subjected to vacuum distillation to give ethyl 2-chloro-2-(4-cyclohexylphenyl)acetate (50 g, yield 89%).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. additionthe residual oil was diluted with water
  4. extractionextracted with ether
  5. washThe ether layer was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationsubjected to vacuum distillation

Sources & evidence

ORD record
ord-47df4bc3843043929b677f82b42a704a
Source dataset
uspto-grants-1991_12
Patent number
US05071841

Reaction notes

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