Ethanol → HCID 13563087, compound

HRID 637316Notes

Reaction equation

HRID 637316 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1.O=[CH:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].[C:16](=[O:19])([O-])[O-].[NH4+:20].[NH4+:21].[C-]#N.[K+].[CH2:25]([OH:27])C>O>[O:27]=[C:25]1[NH:21][C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:16](=[O:19])[NH:20]1

Participants

6

Reactant 4

HCID 702EthanolHCID 9032Potassium CyanideHCID 517111Ammonium Carbonate2×HCID 86740517HCID 86740517, compound

Product 1

HCID 13563087HCID 13563087, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

m-Methoxybenzene-gamma-oxo-butanoic acid (C.A. reg. no. 38102-67-9) (10.0 g, 48 mmol) was combined with 22.75 g (235 mmol) ammonium carbonate, 6.5 g (100 mmol) potassium cyanide in 100 ml ethanol and 100 ml water at 65° C. After 5 hours at 65° C. an additional 22.75 g (235 mmol) ammonium carbonate was added and heating was continued for 18 hours. The reaction mixture was concentrated in vacuo, triturated with water and the acidity was adjusted to pH 4 with concentrated hydrochloric acid. A white solid formed which was collected by filtration and dried in vacuo at 80° C. for 20 hours to give 10.6 g (79% yield) of the title compound: mp 138° C.

Workup

  1. temperatureheating
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customtriturated with water
  4. customA white solid formed which
  5. filtrationwas collected by filtration
  6. customdried in vacuo at 80° C. for 20 hours

Sources & evidence

ORD record
ord-d4fd08415e5441ddb1f7da85012c3012
Source dataset
uspto-grants-1985_12
Patent number
US04556670

Reaction notes

Loading…