Dimethylformamide → HCID 22734018, compound

HRID 2084813Notes

Reaction equation

HRID 2084813 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[CH2:14]1[CH2:20][CH:19](Cl)[C:17](=[O:18])[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[O:1][CH:16]1[CH2:15][CH2:14][CH2:20][CH2:19][C:17]1=[O:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 132032-Chlorocyclohexanone2×HCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 22734018HCID 22734018, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl 3-hydroxy-4-methoxybenzoate (2.47 g), α-chlorocyclohexanone (2.33 ml), potassium carbonate (3.76 g), and DMF (25 ml) was stirred at 90° C. for 2 hours. α-Chlorocyclohexanone (2.0 ml) was further added to the mixture, followed by stirring at 90° C. for one hour. After being allowed to stand for cooling, water was added to the mixture followed by extraction with ether. The organic layer was washed with a 1N aqueous solution of sodium hydroxide and then with a saturated saline, and dried over sodium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (silica gel, hexane:ethyl acetate=2:1) to give Compound IIm-a (3.16 g, 83%) as an oily substance.

Workup

  1. stirringby stirring at 90° C. for one hour
  2. temperaturefor cooling
  3. extractionfollowed by extraction with ether
  4. washThe organic layer was washed with a 1N aqueous solution of sodium hydroxide
  5. dry with materialwith a saturated saline, and dried over sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by column chromatography (silica gel, hexane:ethyl acetate=2:1)
  8. customto give Compound IIm-a (3.16 g, 83%) as an oily substance

Sources & evidence

ORD record
ord-13311dc9791c4646bf46d9196b6e8bd8
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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