Hydrochloric Acid → HCID 14528680, compound

HRID 223719Notes

Reaction equation

HRID 223719 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:9][S:10][C:11]1[CH:12]=[C:13]([CH:17]([CH3:23])[C:18]([O:20]CC)=[O:19])[CH:14]=[CH:15][CH:16]=1)#N.[OH-:24].[K+].Cl.[OH2:27]>C(O)COCCO>[C:1]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:9][S:10][C:11]1[CH:12]=[C:13]([CH:17]([CH3:23])[C:18]([OH:20])=[O:19])[CH:14]=[CH:15][CH:16]=1)([OH:27])=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14797Potassium HydroxideHCID 20520589HCID 20520589, compound

Product 1

HCID 14528680HCID 14528680, compound

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
250 °C

Procedure

The above ester compound (2.6 g) was added to a solution of potassium hydroxide (2.6 g) in water (5 ml) and diethylene glycol (8 ml) and the mixture was heated with stirring for 5.5 hours in an oil bath maintained at 250° C. The reaction mixture was poured into water, acidified with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layers were washed with water, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure to give the title compound (2.5 g) as an oil. IRνmaxfilm cm-1 : 1700 (C=O). MS m/e: 322 (M+).

Workup

  1. temperaturethe mixture was heated
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layers were washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-cc45082acc2a48d893f4dc39c406629a
Source dataset
uspto-grants-1982_10
Patent number
US04356186

Reaction notes

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