Phosgene → Piperonal

HRID 236699Notes

Reaction equation

HRID 236699 reaction equation
[CH2:1]1[O:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2]1.CN([CH:18]=[O:19])C1C=CC=CC=1.C(Cl)(Cl)=O>>[CH2:1]1[O:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2]1.[CH:6]1[C:7]([CH:18]=[O:19])=[CH:8][C:3]2[O:2][CH2:1][O:9][C:4]=2[CH:5]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 92291,3-BenzodioxoleHCID 66737N-Methylformanilide

Product 2

HCID 8438PiperonalHCID 92291,3-Benzodioxole

Conditions

Temperature
70 °C

Procedure

Into a mixture of 97.7 g (0.80 mole) of 1,2-methylenedioxybenzene and 108 g (0.80 mole) of N-methylformanilide was introduced 80.0 g (0.81 mole) of phosgene at 50° C. over a 1-hour period. Then, the reaction mixture was heated at 70° C. for 5 hours, poured into ice water, and allowed to stand for 1 hour. Thereafter, the resulting mixture was treated in the same manner as in Example 1 to obtain 48.0 g (0.393 mole) of 1,2-methylenedioxybenzene and 58.9 g (0.392 mole) of piperonal. The yield and selectivity of piperonal were 49.0% and 96.3%, respectively. The recoveries of N-methylaniline and N-methylformanilide were 64.2% and 2.3%, respectively.

Workup

  1. additionThereafter, the resulting mixture was treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-a9aed8f06ad74d64baca358392fc3ebb
Source dataset
uspto-grants-1979_06
Patent number
US04157333

Reaction notes

Loading…