Hydrogen Cyanide → 3-hydroxy-3-cyano-3,4-dihydro-2H-1,5-benzodioxepin

HRID 267767

Reaction equation

HRID 267767 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][CH2:3]1.[CH:13]#[N:14].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[OH:1][C:2]1([C:13]#[N:14])[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 768Hydrogen 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 241BenzeneSolvent2×

Procedure

To a stirred solution of 4.92 g. (30 millimoles) of 3-oxo-3,4-dihydro-2H-1,5-benzodioxepin in 100 mls. of benzene is added dropwise a solution of 30 millimoles of anhydrous hydrogen cyanide in 50 ml. of benzene. The reaction mixture is stirred overnight at ambient temperature, basified with 10% sodium carbonate solution and the organic layer separated. The benzene solution is washed once with water and dried successively over anhydrous magnesium sulfate and calcium sulfate. Evaporation of the solvent under reduced pressure at 40° C. yields the crude cyanohydrin which upon purification and mixed melting point determination gives no depression with an authentic sample of 3-hydroxy-3-cyano-3,4-dihydro-2H-1,5-benzodioxepin.

Workup

  1. customthe organic layer separated
  2. washThe benzene solution is washed once with water
  3. dry with materialdried successively over anhydrous magnesium sulfate and calcium sulfate
  4. customEvaporation of the solvent under reduced pressure at 40° C.
  5. customyields the crude cyanohydrin which
  6. customupon purification
  7. additionmixed

Sources & evidence

ORD record
ord-e6799d215004407bbdec444fa4284f11
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Linked notes

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