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

HRID 1030679노트

반응식

HRID 1030679 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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. additionThen, 800 ml of hexane was added to the obtained residue
  7. customthe hexanesoluble substance was removed by decantation

출처 및 근거

ORD 기록
ord-31774bd6c8594bda97fafc702acff8a2
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05106871

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