Chlorine → 5-Chloro-2,2,6-Trimethyl-1,3-Dioxin-4-One

HRID 1249631Notes

Reaction equation

HRID 1249631 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH:5]=[C:4]([CH3:9])[O:3]1.[Cl:11]Cl>C(Cl)Cl>[Cl:11][C:5]1[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]=1[CH3:9]

Participants

4

Reactant 2

HCID 24526ChlorineHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

Product 1

HCID 135878355-Chloro-2,2,6-Trimethyl-1,3-Dioxin-4-OneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 2,2,6-trimethyl-4H-1,3-dioxin-4-one (0.2 mol, 28.4 g) in 100 ml of CH2Cl2 was cooled to -50° C. and liquid chlorine (0.25 mol) was added dropwise over five minutes. The solution was allowed to warm to 20° C. over 30 minutes, and the solvent was then removed in vacuo, leaving 35.8 g (100% yield, 92% assay) of a pale yellow oil. A portion of this mixture was purified by flash chromatography (10% Et2O/hexanes on silica) to provide the title compound as white crystals.

Workup

  1. customthe solvent was then removed in vacuo
  2. customleaving 35.8 g (100% yield, 92% assay) of a pale yellow oil
  3. customA portion of this mixture was purified by flash chromatography (10% Et2O/hexanes on silica)

Sources & evidence

ORD record
ord-3955d3ec31914e04b111ffd660342868
Source dataset
uspto-grants-1986_12
Patent number
US04633013

Reaction notes

Loading…