Chloroacetaldehyde → 4,5,6,7-Tetrahydro-1-benzofuran-4-one

HRID 637782Notes

Reaction equation

HRID 637782 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:16][CH:17]=O>O>[O:7]=[C:3]1[C:2]2[CH:16]=[CH:17][O:8][C:1]=2[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 104341,3-CyclohexanedioneHCID 11430Potassium Carbonate

Product 1

HCID 27335414,5,6,7-Tetrahydro-1-benzofuran-4-oneYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1.12 g (10 mmoles) of 1,3-cyclohexanedione and 8 ml of water was added 1.38 g (10 mmoles) of potassium carbonate, and then 2 ml of 40% aqueous solution of chloroacetaldehyde was added thereto. The resulting mixture was stirred at a room temperature for 45 hours. The reaction mixture was maintained at a pH of from 7.75 to 9.50 throughout the reaction. After completing the reaction, the obtained reaction mixture was treated and analyzed in the same manner as in Example 1. It was proved from the results of the analysis that 4-oxo-4,5,6,7-tetrahydrobenzofuran was produced in a 68% yield.

Workup

  1. temperatureThe reaction mixture was maintained at a pH of from 7.75 to 9.50 throughout the reaction
  2. customthe reaction
  3. customthe obtained reaction mixture
  4. additionwas treated

Sources & evidence

ORD record
ord-3acf00d91bd24845bfb054d1ec170446
Source dataset
uspto-grants-1985_12
Patent number
US04558143

Reaction notes

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