Hydrochloric Acid → 2H-1,5-Benzodioxepin-3(4H)-one

HRID 267788Notes

Reaction equation

HRID 267788 reaction equation
[O:1]=[C:2]1[CH2:8][O:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4][CH:3]1C(OC)=O.CO.Cl>O>[O:1]=[C:2]1[CH2:3][O:4][C:5]2[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=2[O:7][CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 13544514methyl 3-oxo-3,4-dihydro-2H-1,5-benzodioxepin-2-carboxylate

Product 1

HCID 113097002H-1,5-Benzodioxepin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Oxo-4-carbomethoxy-3,4-dihydro-2H-1,5-benzodioxepin (110 g.) is added to a mixture of methanol (210 ml.), concentrated hydrochloric acid (50 ml.) and water (160 ml.) and the mixture then is refluxed for 18 hours. The product is extracted with ether, and the ether extract washed with four 50 ml. portions of sodium bicarbonate solution, then twice with 50 ml. portions of water. After drying the washed ether extract over magnesium sulfate and evaporation to remove the solvent there is obtained 3-oxo-3,4-dihydro-2H-1,5-benzodioxepin.

Workup

  1. temperaturethe mixture then is refluxed for 18 hours
  2. extractionThe product is extracted with ether
  3. extractionthe ether extract
  4. washwashed with four 50 ml
  5. dry with materialAfter drying the washed ether
  6. extractionextract over magnesium sulfate and evaporation
  7. customto remove the solvent there

Sources & evidence

ORD record
ord-44c56e48478045f3aa81d409068f6f02
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Reaction notes

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