Acetone → HCID 22494013, compound

HRID 1435144Notes

Reaction equation

HRID 1435144 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].C(=O)([O-])[O-].[K+].[K+].S(OCC)(O[CH2:22][CH3:23])(=O)=O.[CH3:27][C:28](C)=O>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:22][CH3:23])=[O:7])=[C:4]([O:11][CH2:27][CH3:28])[CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 787824-Chlorosalicylic acid

Product 1

HCID 22494013HCID 22494013, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chlorosalicylic acid (10.0 g, 57.94 mmol) and potassium carbonate (80 g, 0.58 mol) and diethyl sulphate (18.76 g, 0.122 mol) in acetone (150 ml) is heated at reflux with stirring for 24 h. The suspension is cooled and diluted with water (200 ml). Extract with diethyl ether (2×) and wash the extracts with water (2×) and brine. The organic phase is dried over magnesium sulphate, filtered and evaporated to a brown oil. The oil is purified using the combiflash on a 120 g silica cartridge eluting with isohexane-ethyl acetate (0 to 25% over 30 min.) to give ethyl 4-chloro-2-ethoxybenzoate as a colourless oil.

Workup

  1. temperatureis heated
  2. temperatureat reflux
  3. temperatureThe suspension is cooled
  4. extractionExtract with diethyl ether (2×)
  5. washwash the extracts with water (2×) and brine
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated to a brown oil
  9. customThe oil is purified
  10. washeluting with isohexane-ethyl acetate (0 to 25% over 30 min.)

Sources & evidence

ORD record
ord-f48fffba2b9d4d468759770fcfd69cdb
Source dataset
uspto-grants-2009_11
Patent number
US07615648B2

Reaction notes

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