Dimethylformamide → Ethyl 3-methoxy-4-cyclohexylphenylglyoxylate

HRID 1863222Notes

Reaction equation

HRID 1863222 reaction equation
[H-].[Na+].[CH3:3]N(C)C=O.[OH:8][C:9]1[CH:10]=[C:11]([C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.CI>O>[CH3:3][O:8][C:9]1[CH:10]=[C:11]([C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20515140HCID 20515140, compound

Product 1

HCID 20515180Ethyl 3-methoxy-4-cyclohexylphenylglyoxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of 0.01 moles of sodium hydride in 25 ml. of dry dimethylformamide 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-5758e800862a44388c4c6ae9f5f4f2b7
Source dataset
uspto-grants-1979_09
Patent number
US04168320

Reaction notes

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