Dimethylformamide → Ethyl 3-methoxy-4-cyclohexylphenylglyoxylate

HRID 839648Notes

Reaction equation

HRID 839648 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([C:16](=[O:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[CH3:23]N(C)C=O.CI>O>[CH3:23][O:3][C:4]1[CH:5]=[C:6]([C:16](=[O:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20515140HCID 20515140, compound

Product 1

HCID 20515180Ethyl 3-methoxy-4-cyclohexylphenylglyoxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 0.01 moles of sodium hydride in 25 ml. of dry dimthylformamide which has been cooled to 0° C is added dropwise a solution of 0.01 moles of ethyl 3-hydroxy-4-cyclohexylphenylglyoxylate in 10 ml. of dimethylformamide. The reaction mixture is stirred for 15 minutes and 0.015 moles of methyliodide is then added dropwise. The mixture is allowed to stir overnight at room temperature. 200 ml. of water is added and the resulting mixture is extracted well with ether. The ether extract is washed with water, dried over sodium sulfate, evaporated to dryness and distilled to obtain ethyl 3-methoxy-4-cyclohexylphenylglyoxylate.

Workup

  1. stirringto stir overnight at room temperature
  2. extractionthe resulting mixture is extracted well with ether
  3. extractionThe ether extract
  4. washis washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. distillationdistilled

Sources & evidence

ORD record
ord-14af745a8f79464981f834f9bd01921d
Source dataset
uspto-grants-1978_06
Patent number
US04096279

Reaction notes

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