Water → HCID 22760935, compound

HRID 1605642Notes

Reaction equation

HRID 1605642 reaction equation
[C:1]([CH:3]1[CH2:21][CH2:20][C:6]2[C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:5]=2[CH2:4]1)#N.[OH2:22].C(O)C[O:25]CCO>[OH-].[K+]>[C:1]([CH:3]1[CH2:21][CH2:20][C:6]2[C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:5]=2[CH2:4]1)([OH:25])=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 8117Diethylene GlycolHCID 22760938HCID 22760938, compound2×

Product 1

HCID 22760935HCID 22760935, compound

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

1.5 g of 2-cyano-1,2,3,4-tetrahydro-tribenzo(b,d,f)-oxepine ("starting material 6") is suspended in 80 ml diethyleneglycol and 65 ml of an aqueous KOH solution (40%). The mixture is refluxed for 5 hours. After cooling the mixture to ambient temperature, it is poured into 450 ml water. The aqueous mixture is extracted with ether to remove non-acidic material. The water-phase is acidified to about pH 3, whereupon the mixture is extracted with ether. The ether extracts are washed, dried and then evaporated, yielding 0.80 g of the crude 2-carboxy-1,2,3,4-tetrahydro-tribenzo(b,d,f)-oxepine. This carboxyl-compound is converted into the dimethylamide in the usual manner and then reduced with LiAlH4, yielding 0.5 g of the title product as an oil.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. extractionThe aqueous mixture is extracted with ether
  3. customto remove non-acidic material
  4. extractionis extracted with ether
  5. washThe ether extracts are washed
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-9570724a2f82400db24856936f71b812
Source dataset
uspto-grants-1976_04
Patent number
US03950425

Reaction notes

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