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

HRID 428150Notes

Reaction equation

HRID 428150 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-f6670f5139694a33b202bf9c2591c4b0
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Reaction notes

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