Chloroacetaldehyde → 6,6-Dimethyl-6,7-dihydro-1-benzofuran-4(5H)-one

HRID 637785Notes

Reaction equation

HRID 637785 reaction equation
Cl[CH2:2][CH:3]=[O:4].C(=O)([O-])O.[Na+].[CH3:10][C:11]1([CH3:19])[CH2:16][C:15](=O)[CH2:14][C:13](=[O:18])[CH2:12]1>O>[O:4]=[C:3]1[C:14]2[CH:15]=[CH:16][O:18][C:13]=2[CH2:12][C:11]([CH3:19])([CH3:10])[CH2:2]1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 31358DimedoneHCID 516892Sodium Bicarbonate2×

Product 1

HCID 15232266,6-Dimethyl-6,7-dihydro-1-benzofuran-4(5H)-oneYield 48.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 24 ml of water and 6 ml of 40% aqueous solution of chloroacetaldehyde was added 0.7 g (8 mmoles) of sodium hydrogencarbonate while cooling with ice. To the reaction mixture were added dropwise 4.2 g (30 mmoles) of 5,5-dimethyl-1,3-cyclohexanedione and 40 ml of aqueous solution containing 2.3 g (27 mmoles) of sodium hydrogencarbonate while cooling with ice at a rate of 0.4 ml/minute. The reaction mixture was maintained at a pH of from 5.7 to 8.0 throughout the reaction. After completing the dropping, the reaction mixture was stirred at a room temperature overnight, and then treated in the same manner as in Example 1 to give 2.36 g (yield: 48.2%) of 4-oxo-6,6-dimethyl-4,5,6,7-tetrahydrobenzofuran being a colorless oily material (boiling point: 78° C./0.7 mmHg).

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewhile cooling with ice at a rate of 0.4 ml/minute
  3. temperatureThe reaction mixture was maintained at a pH of from 5.7 to 8.0 throughout the reaction
  4. additiontreated in the same manner as in Example 1

Sources & evidence

ORD record
ord-736faf24ebc949068c09db59ef60f882
Source dataset
uspto-grants-1985_12
Patent number
US04558143

Reaction notes

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