Phosgene → 3,4-Dihydro-2H-pyran-3-carbonyl chloride

HRID 1077666Notes

Reaction equation

HRID 1077666 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[O:5]1[CH2:10][CH2:9][CH2:8][CH:7]=[CH:6]1>C1(C)C=CC=CC=1>[O:5]1[CH:6]=[CH:7][CH2:8][CH:9]([C:1]([Cl:4])=[O:2])[CH2:10]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 80803,4-dihydro-2H-pyran

Product 1

HCID 194320763,4-Dihydro-2H-pyran-3-carbonyl chlorideYield 56,709.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

125 g (1.25 mmol) of phosgene gas were introduced over the course of 2.5 hours at 45°-50° C. into a solution of 84 g (1 mol) of 5,6-dihydro-4H-pyran in 50 g of toluene. The mixture was subsequently stirred at 60° C. for a further 5 hours. Work-up was carried out as described in Example 1. Vacuum distillation at 76° C./1 mbar gave 103.9 g (80%) of valuable product.

Workup

  1. distillationVacuum distillation at 76° C./1 mbar

Sources & evidence

ORD record
ord-86668c48ab854345a5c1d4ed7ba6fd02
Source dataset
uspto-grants-1996_08
Patent number
US05543568

Reaction notes

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