Sodium Carbonate → 3,4-Dihydro-7-methoxy-1-benzoxepin-5(2H)-one oxime

HRID 1448062Notes

Reaction equation

HRID 1448062 reaction equation
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[Na+].[Na+].[CH3:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[O:21][CH2:20][CH2:19][CH2:18][C:17](=O)[C:16]=2[CH:23]=1>O.C(O)C>[CH3:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[O:21][CH2:20][CH2:19][CH2:18][C:17](=[N:2][OH:3])[C:16]=2[CH:23]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 135224797-METHOXY-2,3,4,5-TETRAHYDRO-1-BENZOXEPIN-5-ONE

Product 1

HCID 858439913,4-Dihydro-7-methoxy-1-benzoxepin-5(2H)-one oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

6.95 g of hydroxylamine hydrochloride dissolved in 15 ml of water and 5.3 g of sodium carbonate are added to a solution of 19.2 g of 7-methoxy-3,4-dihydro-1-benzoxepin-5-one in 45 ml of ethanol. The mixture is left at room temperature for 24 hours with stirring. 100 ml of water are then added and the alcohol is evaporated. The aqueous solution is make alkaline by the addition of soda and unreacted benzoxepin is extracted with ether. The aqueous phase is neutralised and the desired oxime is extracted with ether. After drying of the organic solution and evaporation of the solvent under reduced pressure, a white solid is obtained which, when recrystallised from cyclohexane yields 17 g of the desired pure product which has a melting point of 103° to 104° C.

Workup

  1. customthe alcohol is evaporated
  2. additionby the addition of soda and unreacted benzoxepin
  3. extractionis extracted with ether
  4. extractionthe desired oxime is extracted with ether
  5. customAfter drying of the organic solution and evaporation of the solvent under reduced pressure
  6. customa white solid is obtained which, when
  7. customrecrystallised from cyclohexane
  8. customyields 17 g of the desired pure product which

Sources & evidence

ORD record
ord-9b4b12e384c74b5285ea963e701d317f
Source dataset
uspto-grants-1979_12
Patent number
US04179516

Reaction notes

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