Hydrochloric Acid → HCID 19854193, compound

HRID 1649632Notes

Reaction equation

HRID 1649632 reaction equation
[C:1]([C:6]1[C:7](=[O:21])[CH2:8][CH2:9][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=2)[C:11]=1[OH:12])(=[O:5])[CH2:2][CH2:3][CH3:4].[Cl-].[Al+3].[Cl-].[Cl-].[C:26](Cl)(=[O:28])[CH3:27].Cl>ClC(Cl)C>[C:1]([C:6]1[C:7](=[O:21])[CH2:8][CH2:9][CH:10]([C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[C:17]([C:26](=[O:28])[CH3:27])[CH:18]=2)[C:11]=1[OH:12])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 198541893-Hydroxy-4-(4-methoxyphenyl)-2-(1-oxobutyl)-2-cyclohexen-1-one

Product 1

HCID 19854193HCID 19854193, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent3×

Procedure

2-Butyryl-3-hydroxy-4-(4-methoxyphenyl)cyclohex-2-ene-1-one (7.1 g) in dichloroethane (35 ml) was added to a suspension of aluminium chloride (10.5 g) in dichloroethane (50 ml) at 0° C. After stirring for 1/2 hour, a solution of acetyl chloride (2.2 g) in dichloroethane (25 ml) was added dropwise. After stirring a further 1/2 hour at 0° C., the reaction mixture was allowed to come to room temperature and poured into cold 5N hydrochloric acid (50 ml). The aqueous solution was then extracted with dichloromethane. The extracts were dried over magnesium sulphate and evaporated in vacuo to give a red oil. Purification on a silica gel column using 5% (v/v) diethylether-dichloromethane as eluant gave the title compound (1.3 g) as a clear oil.

Workup

  1. stirringAfter stirring a further 1/2 hour at 0° C.
  2. customto come to room temperature
  3. extractionThe aqueous solution was then extracted with dichloromethane
  4. dry with materialThe extracts were dried over magnesium sulphate
  5. customevaporated in vacuo
  6. customto give a red oil
  7. customPurification on a silica gel column

Sources & evidence

ORD record
ord-fb00cdbf88044f34a6dee99dc944136b
Source dataset
uspto-grants-1990_05
Patent number
US04921524

Reaction notes

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