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

HRID 2254200Notes

Reaction equation

HRID 2254200 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'-prenylacetophenoneYield 45.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 750 ml of tetrahydrofuran was dissolved 149.95 g of 2',4'-dihydroxyacetophenone, and 409.26 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, 3 N hydrochloric acid was added to the reaction liquid under cooling to make the aqueous layer acidic, and the aqueous layer was extracted with ether. The ether extract was washed with water and dried with anhydrous sodium sulfate and the solvent was removed by distillation. Then, 800 ml of hexane was added to the obtained residue and the hexane-soluble substances were removed by decantation to obtain 98.55 g (yield=45.4%) of 2',4'-dihydroxy-3'-(3-methyl-2-butenyl)acetophenone in the form of a colorless solid.

Workup

  1. additionwere added to the solution
  2. additionwas added to the reaction liquid
  3. temperatureunder cooling
  4. extractionthe aqueous layer was extracted with ether
  5. extractionThe ether extract
  6. washwas washed with water
  7. dry with materialdried with anhydrous sodium sulfate
  8. customthe solvent was removed by distillation
  9. additionThen, 800 ml of hexane was added to the obtained residue
  10. customthe hexane-soluble substances were removed by decantation

Sources & evidence

ORD record
ord-46c4b2d03b6c47eea626bd75ff00d8cc
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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