Hydrochloric Acid → HCID 13726873, compound

HRID 1583882Notes

Reaction equation

HRID 1583882 reaction equation
C(OCC)(=O)[CH2:2][C:3](OCC)=[O:4].[Na].[CH3:13][S:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[CH:22][C:23](=[O:25])[CH3:24])=[CH:17][CH:16]=1.[OH-].[K+].Cl>C(O)C.O>[OH:4][C:3]1[CH2:2][CH:21]([C:18]2[CH:19]=[CH:20][C:15]([S:14][CH3:13])=[CH:16][CH:17]=2)[CH2:22][C:23](=[O:25])[CH:24]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 14797Potassium HydroxideHCID 5360545SodiumHCID 544426034-[4-(Methylsulfanyl)phenyl]but-3-en-2-one

Product 1

HCID 13726873HCID 13726873, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Diethyl malonate (7.3 g; 45.4 mmole) was added to a solution of sodium metal (1.0 g; 42.9 mmole) in anhydrous absolute ethanol (100 ml). 1-(4-Methylthiophenyl)but-1-en-3-one (9.0 g; 43.7 mmole) was added to the solution and the mixture was heated under reflux, under nitrogen, with stirring for a period of 4 hours. An aqueous solution of potassium hydroxide (5.3 g in 30 ml of water) was added and the mixture was heated under reflux for a further 4 hours. The solution was poured into water, acidified with dilute aqueous hydrochloric acid and extracted with ethyl acetate. The organic phase was extracted with an aqueous 10% sodium hydroxide solution, the aqueous extract was acidified with dilute aqueous hydrochloric acid extracted with ethyl acetate. The organic phase was washed with with water, dried over anhydrous sodium sulfate and the solvent was evaporated to give 3-hydroxy-5-(4-methylthiophenyl)cyclohex-2-en-1-one (7.6 g) as a yellow crystalline solid, mp 199° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux, under nitrogen
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for a further 4 hours
  5. extractionextracted with ethyl acetate
  6. extractionThe organic phase was extracted with an aqueous 10% sodium hydroxide solution
  7. extractionthe aqueous extract
  8. extractionextracted with ethyl acetate
  9. washThe organic phase was washed with with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6b06085953fd44ce9c76566db529b8d1
Source dataset
uspto-grants-1985_11
Patent number
US04555263

Reaction notes

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