Thionyl Chloride → 4,6-Dimethyl-3,4-dihydro-2h-pyran-2-one

HRID 1891991Notes

Reaction equation

HRID 1891991 reaction equation
[CH3:1][CH:2]([CH2:7][C:8](=[O:10])[CH3:9])[CH2:3][C:4]([OH:6])=O.S(Cl)(Cl)=O>C1C=CC=CC=1>[CH3:1][CH:2]1[CH:7]=[C:8]([CH3:9])[O:10][C:4](=[O:6])[CH2:3]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 102612073-Methyl-5-oxohexanoic acid

Product 1

HCID 2818574,6-Dimethyl-3,4-dihydro-2h-pyran-2-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 3-methyl-5-oxohexanoic acid (2.1 g) in benzene (26 mL) was treated at rt with thionyl chloride (1.26 mL). The mixture was heated to 85° C. where it stirred for 2 days. At the conclusion of this period, the mixture was cooled to rt and concentrated under vacuum to provide 4,6-dimethyl-3,4-dihydropyran-2-one as a dark brown oil, which was used directly in Step 4 without purification. Mass spectrum m/z 127.37 (M+H+).

Workup

  1. temperatureAt the conclusion of this period, the mixture was cooled to rt
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-80270d6cf1334433aa682efef6cfb69d
Source dataset
uspto-grants-2013_08
Patent number
US08507559B2

Reaction notes

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