Acetic Anhydride → 3-hydroxy-3-cyano-3,4-dihydro-2H-1,5-benzodioxepin

HRID 267766Notes

Reaction equation

HRID 267766 reaction equation
[C-:1]#[N:2].[K+].[O:4]=[C:5]1[CH2:11][O:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[O:7][CH2:6]1.C(OC(=O)C)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[OH:4][C:5]1([C:1]#[N:2])[CH2:6][O:7][C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[O:10][CH2:11]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 9032Potassium CyanideHCID 10340Sodium CarbonateHCID 113097002H-1,5-Benzodioxepin-3(4H)-one

Product 1

HCID 155572933-hydroxy-3-cyano-3,4-dihydro-2H-1,5-benzodioxepin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 13.5 g. (208 millimoles) of potassium cyanide in 27 ml. of water is added dropwise to a mixture of 18.7 g. (114 millimoles) of 3-oxo-3,4-dihydro-2H-1,5-benzodioxepin and 21.2 g. (208 millimoles) of acetic anhydride with stirring and cooling. The mixture is stirred at ambient temperature overnight and then is made alkaline with 10% sodium carbonate solution. The product in the form of an oil is extracted with diethyl ether, treated with charcoal and dried over calcium sulfate. Evaporation of the solvent gives a solid that is recrystallized from carbon tetrachloride to give 3-hydroxy-3-cyano-3,4-dihydro-2H-1,5-benzodioxepin as plates, m.p. 108.5°-110° C.

Workup

  1. temperaturecooling
  2. extractionThe product in the form of an oil is extracted with diethyl ether
  3. additiontreated with charcoal
  4. dry with materialdried over calcium sulfate
  5. customEvaporation of the solvent
  6. customgives a solid
  7. customthat is recrystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-8fc40df85f644bf1842db4225c025993
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Reaction notes

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