Water → 7-Methoxy-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde

HRID 394646Notes

Reaction equation

HRID 394646 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:11]2[O:12][CH2:13][CH2:14][O:15][C:10]=2[CH:9]=1.O.CN([CH:22]=[O:23])C>>[CH3:6][O:7][C:8]1[C:17]([CH:22]=[O:23])=[CH:16][C:11]2[O:12][CH2:13][CH2:14][O:15][C:10]=2[CH:9]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 109099186-Methoxy-2,3-dihydrobenzo[b][1,4]dioxine

Product 1

HCID 64970647-Methoxy-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde

Procedure

3.3 eq. of dry DMF are placed in a three-necked flask and then, using a dropping funnel, 1.3 eq. of phosphorus oxychloride are added at 0° C. After returning to ambient temperature, the compound obtained in Step B (4 g: 20.59 mmol) is dissolved in 6.5 ml of DMF and then added to the previous solution. Heating is carried out for 2 hours at 110° C. After cooling, the mixture is hydrolysed with water and extracted with dichloromethane.

Workup

  1. customAfter returning to ambient temperature
  2. additionadded to the previous solution
  3. temperatureHeating
  4. temperatureAfter cooling
  5. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-4e325a1e4090449ca4b7eef222c36685
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

Loading…