Hydrochloric Acid → HCID 178458841, compound

HRID 235601Notes

Reaction equation

HRID 235601 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH:13]1[CH2:18][C:17](=[O:19])[C:16]([C:20](=[O:23])[CH2:21][CH3:22])=[C:15]([OH:24])[CH2:14]1.[Cl-].[Cl-].[Cl-].[Al+3].[C:29](Cl)(=[O:31])[CH3:30].Cl>ClCCCl>[C:29]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:13]2[CH2:18][C:17](=[O:19])[C:16]([C:20](=[O:23])[CH2:21][CH3:22])=[C:15]([OH:24])[CH2:14]2)=[C:2]([CH3:1])[C:11]=1[CH3:12])(=[O:31])[CH3:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 178458833HCID 178458833, compound

Product 1

HCID 178458841HCID 178458841, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 5-(2,3-dimethylnaphth-1-yl)-3-hydroxy-2-propionylcyclohex-2-en-1-one (1.7 g; 5.3 mmol) in 1,2-dichloroethane (5 ml) was added to a suspension of aluminium trichloride (2.2 g; 16.75 mmol) in 1,2-dichloroethane (10 ml) at 0° C. The mixture was stirred at 0° C. for 30 min and a solution of acetyl chloride (0.5 g; 6.36 mmol) in 1,2-dichloroethane (5 ml) was added. After stirring at 0° C. for 30 min and at room temperature for 2 hr, the mixture was poured into a cold aqueous 50% hydrochloric acid solution which was then stirred vigorously for 1 hr. The solution was extracted with dichloromethane and the organic phase was washed with water. The dried (MgSO4) organic fraction was evaporated and the residue was purified by preparative thin-layer chromatography with dichloromethane/ethyl acetate (2:1 v/v) elution to give 5-[4-acetyl-2,3-dimethylnaphth- 1-yl]-3-hydroxy-2-propionylcyclohex-2-en-1-one as a yellow oil.

Workup

  1. stirringAfter stirring at 0° C. for 30 min and at room temperature for 2 hr
  2. stirringwas then stirred vigorously for 1 hr
  3. extractionThe solution was extracted with dichloromethane
  4. washthe organic phase was washed with water
  5. dry with materialThe dried (MgSO4) organic fraction
  6. customwas evaporated
  7. customthe residue was purified by preparative thin-layer chromatography with dichloromethane/ethyl acetate (2:1 v/v) elution

Sources & evidence

ORD record
ord-c0b8580c720f46118ec0a9689d563886
Source dataset
uspto-grants-1987_02
Patent number
US04640708

Reaction notes

Loading…