Hydrochloric Acid → HCID 19854191, compound

HRID 1649629Notes

Reaction equation

HRID 1649629 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][C:8]2=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][CH2:16][CH2:17][C:18](Cl)=[O:19].Cl>[Cl-].[Zn+2].[Cl-].N1C=CC=CC=1>[C:18]([C:9]1[C:10](=[O:13])[CH2:11][CH2:12][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]=1[OH:14])(=[O:19])[CH2:17][CH2:16][CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8855Butyryl chlorideHCID 41815734-phenylcyclohexane-1,3-dione

Product 1

HCID 19854191HCID 19854191, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1049PyridineSolvent

Procedure

Zinc chloride (7.1 g) was added to pyridine (50 ml) followed by 4-phenylcyclohexane-1,3-dione (5 g). n-Butyryl chloride (2.6 g) was then added dropwise and the mixture heated to reflux for 4 hours. After cooling, the mixture was poured into 5N hydrochloric acid (200 ml) and the aqueous phase extracted with methylene chloride. The extracts were dried over magnesium sulphate, filtered and evaporated to give a red oil. Purification on a silica gel column using methylene chloride as eluent gave the title compound as an orange oil (2.15 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter cooling
  4. extractionthe aqueous phase extracted with methylene chloride
  5. dry with materialThe extracts were dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a red oil
  9. customPurification on a silica gel column

Sources & evidence

ORD record
ord-5f076e194ed84c399862ec194f5a041c
Source dataset
uspto-grants-1990_05
Patent number
US04921524

Reaction notes

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