Hydrochloric Acid → HCID 178458850, compound

HRID 2291233Notes

Reaction equation

HRID 2291233 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][C:6]1[CH2:11][CH:10]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[C:14]([CH2:20][C:21]#[N:22])[C:13]=2[CH3:23])[CH2:9][C:8](=[O:24])[C:7]=1[C:25](=[O:28])[CH2:26][CH3:27].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(=S)=S>[OH:5][C:6]1[CH2:11][CH:10]([C:12]2[C:13]([CH3:23])=[C:14]([CH2:20][C:21]#[N:22])[C:15]([CH3:19])=[C:16]([C:1](=[O:3])[CH3:2])[C:17]=2[CH3:18])[CH2:9][C:8](=[O:24])[C:7]=1[C:25](=[O:28])[CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 178458837HCID 178458837, compound

Product 1

HCID 178458850HCID 178458850, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Acetyl chloride (1.34 g, 17.0 mmol) was added to an ice cooled mixture of 3-hydroxy-2-propionyl-5-(3-cyanomethyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (2.65 g, 8.15 mmol) and aluminium chloride (4.15 g, 33.4 mmol) in carbon disulfide (100 ml). The mixture was refluxed for 4 h, cooled and added cautiously to 10% hydrochloric acid (50 ml) and ice (50 ml). The organic solvent was allowed to evaporate from the mixture then the aqueous layer was extracted with ethyl acetate, the organic extracts were washed with water, dried over sodium sulfate and concentrated under reduced pressure. The crude product was chromatographed on silica gel (elution with an increasing gradient of ethyl acetate in methylene chloride). After an initial fraction of unreacted starting material, 3-hydroxy-2-propionyl-5-(3-acetyl-5-cyanomethyl-2,4,6-trimethyl phenyl)cyclohex-2-en-1-one was obtained as a colourless solid (1.5 g, 50%), which was characterized by proton magnetic resonance spectroscopy (CDCl3 ; δ in ppm): 1.12 (3H,t); 2.23 (3H,s); 2.25 (3H,s); 2.47 (6H,s); 2.4-4.1 (7H,m); 18.08 (1H,s).

Workup

  1. temperaturecooled
  2. temperatureThe mixture was refluxed for 4 h
  3. temperaturecooled
  4. customto evaporate from the mixture
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washthe organic extracts were washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was chromatographed on silica gel (
  10. washelution with an increasing gradient of ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-1cda14df20bc4dc6a0c849b02ad7aebf
Source dataset
uspto-grants-1989_01
Patent number
US04795487

Reaction notes

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