1,4-Benzodioxane-2-methanol → 2-(Chloromethyl)-2,3-dihydro-1,4-benzodioxin

HRID 2417797Notes

Reaction equation

HRID 2417797 reaction equation
O[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.S(Cl)([Cl:15])=O>N1C=CC=CC=1>[Cl:15][CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1

Participants

4

Reactant 2

HCID 193141,4-Benzodioxane-2-methanolHCID 24386Thionyl Chloride

Product 1

HCID 953202-(Chloromethyl)-2,3-dihydro-1,4-benzodioxin

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.42 mole of 2-hydroxymethyl-1,4-benzodioxane, 0.42 mole of thionyl chloride and 600 ml of dry pyridine were heated at 100° C. for 3 hours. After the mixture had been cooled, ice-cold dilute hydrochloric acid was added and the mixture was extracted with ether. After drying, the solvent was removed and the residue was distilled in vacuo. Boiling point: 80° C. (0.9 mbar).

Workup

  1. temperatureAfter the mixture had been cooled
  2. additionice-cold dilute hydrochloric acid was added
  3. extractionthe mixture was extracted with ether
  4. customAfter drying
  5. customthe solvent was removed
  6. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-5c1562810d924c81a6c2eaee24bdcede
Source dataset
uspto-grants-1984_09
Patent number
US04470989

Reaction notes

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