Thionyl Chloride → 3,4-Dihydro-4,4-dimethyl-2H-pyran-2-one

HRID 225028Notes

Reaction equation

HRID 225028 reaction equation
[CH3:1][C:2]([CH3:10])([CH2:7][CH:8]=[O:9])[CH2:3][C:4](O)=[O:5].S(Cl)(Cl)=O>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:10])[CH:7]=[CH:8][O:9][C:4](=[O:5])[CH2:3]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 30187243,3-Dimethyl-5-oxopentanoic acid

Product 1

HCID 30186853,4-Dihydro-4,4-dimethyl-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1.05 g (7.28 mmol) of crude 3,3-dimethyl-5-oxopentanoic acid (from Example 8a) and 1 g (8.4 mmol) of thionyl chloride in 10 mL of benzene was heated under reflux for 62/3 hours. The reaction mixture was concentrated to give 3,4-dihydro-4,4-dimethyl-2H-pyran-2-one. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureunder reflux for 62/3 hours
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-a771fe6897e64e00a5469edfd61e7082
Source dataset
uspto-grants-1980_11
Patent number
US04235780

Reaction notes

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