Acetic Acid → Cyclohexanecarboxylic acid (4-oxo-butyl)-amide

HRID 1942350Notes

Reaction equation

HRID 1942350 reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][CH2:7][NH:8][C:9]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])C.C(O)(=O)C.Cl>C(O)C>[O:3]=[CH:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 66937511Cyclohexanecarboxylic acid (4,4-diethoxy-butyl)-amide

Product 1

HCID 85725969Cyclohexanecarboxylic acid (4-oxo-butyl)-amide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.09 g (4 mmol) 20A, 5 mL acetic acid, 2.5 mL 1N aqueous hydrochloric acid and 20 mL ethanol are put together and stirred for 16 hours under argon atmosphere. Ethanol is evaporated. Then the resulting residue is dispersed in dichloromethane and extracted with saturated sodium bicarbonate solution. The organic phase is dried with sodium sulfate and the solvent evaporated in vacuum. The crude product is obtained in almost quantitative yield.

Workup

  1. customEthanol is evaporated
  2. additionThen the resulting residue is dispersed in dichloromethane
  3. extractionextracted with saturated sodium bicarbonate solution
  4. dry with materialThe organic phase is dried with sodium sulfate
  5. customthe solvent evaporated in vacuum

Sources & evidence

ORD record
ord-39c617570c8b42f4a0ef98416660f378
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

Loading…