Hydrochloric Acid → 2',4'-dihydroxy-3'-prenylacetophenone

HRID 2254194Notes

Reaction equation

HRID 2254194 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22].Cl>O1CCCC1>[OH:1][C:2]1[C:7]([CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 69902',4'-DihydroxyacetophenoneHCID 104291-Chloro-3-methyl-2-buteneHCID 11430Potassium Carbonate

Product 1

HCID 109329712',4'-dihydroxy-3'-prenylacetophenone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 750 ml of tetrahydrofuran was dissolved 149.9 g of 2',4'-dihydroxyacetophenone, and 409.2 g of anhydrous potassium carbonate and 150 ml of 1-chloro-3-methyl-2-butene were added to the solution and the mixture was stirred at room temperature in a nitrogen current for 5 days. After the reaction, the reaction mixture was made acidic by addition of hydrochloric acid and extracted with diethyl ether. The solvent was removed from the ether extract by distillation Then, 800 ml of hexane was added to the obtained residue and the hexanesoluble substance was removed by decantation to obtain 2',4'-dihydroxy-3'-(3-methyl-2-butenyl)acetophenone in the form of a colorless solid. Then, 19.0 g of the so-obtained solid was dissolved in 160 ml of acetone, and 14.2 g of anhydrous potassium carbonate and 6.2 ml of methyl iodide were added to the solution and the mixture was stirred at room temperature overnight in a nitrogen current. After the reaction, the solvent was removed by distillation and the obtained residue was extracted with diethyl ether. The solvent was removed from the extract by distillation to obtain 20.0 g (yield=99.1%) of 2'-hydroxy-4'-methoxy-3'-(3-methyl-2-butenyl)acetophenone.

Workup

  1. additionwere added to the solution
  2. customAfter the reaction
  3. extractionextracted with diethyl ether
  4. customThe solvent was removed from the ether
  5. extractionextract by distillation
  6. addition800 ml of hexane was added to the obtained residue
  7. customthe hexanesoluble substance was removed by decantation

Sources & evidence

ORD record
ord-0a6fe159a13e47199cb2691544311c34
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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