Acetaldehyde → 1-(p-Prenylphenyl)ethanol

HRID 1903591

반응식

HRID 1903591 반응식
[Mg].C(Br)C.II.Cl[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1.[CH:19](=[O:21])[CH3:20].[Cl-].[NH4+]>O1CCCC1.II>[CH2:14]([C:11]1[CH:12]=[CH:13][C:8]([CH:19]([OH:21])[CH3:20])=[CH:9][CH:10]=1)[CH:15]=[C:16]([CH3:18])[CH3:17]

참가 물질

9

반응물 6

HCID 177AcetaldehydeHCID 807IodineHCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 316460p-ChloroprenylbenzeneHCID 5462224Magnesium

생성물 1

HCID 132172751-(p-Prenylphenyl)ethanol수율 74.9%

시약·촉매·용매 2

HCID 807Iodine촉매HCID 8028Tetrahydrofuran용매4회

실험 절차

Under a nitrogen atmosphere, 9.6 g of magnesium turnings, 30 ml of tetrahydrofuran and about 50 mg of iodine were put in a flask. With stirring, 2 ml of ethyl bromide was added, whereupon coloration by iodine disappeared. With stirring, the mixture was heated and maintained at 110° C. to 120° C., and 60 g of p-chloroprenylbenzene was added. During the reaction, 20 ml of tetrahydrofuran was further added. After continuing the reaction for 4.5 hours, the reaction mixture was cooled to room temperature, and 200 ml of tetrahydrofuran was added. A solution of 22.0 g of acetaldehyde in 30 ml of tetrahydrofuran was added at 5° C. to 10° C. over the course of about 2 hours. After the addition, the mixture was stirred for 1 hour, and then 400 ml of a 10% by weight aqueous solution of ammonium chloride was added. The mixture was separated into an organic layer and an aqueous layer. The aqueous layer was extracted with 30 ml of diethyl ether. The diethyl ether layer was combined with the organic layer previously separated and washed with water, dried, concentrated and distilled to give 47.3 g (yield 74.9%) of 1-(p-prenylphenyl)ethanol having a boiling point of 108° C. to 110° C./0.5 mmHg. The nuclear magnetic resonance spectrum of the product was as follows. (The chemical shifts are expressed in δ (ppm) when hexamethylsiloxane is used as a standard.)

후처리

  1. stirringWith stirring
  2. temperaturethe mixture was heated
  3. temperaturemaintained at 110° C. to 120° C.
  4. additionwas further added
  5. customthe reaction for 4.5 hours
  6. additionAfter the addition
  7. stirringthe mixture was stirred for 1 hour
  8. customThe mixture was separated into an organic layer
  9. extractionThe aqueous layer was extracted with 30 ml of diethyl ether
  10. custompreviously separated
  11. washwashed with water
  12. customdried
  13. concentrationconcentrated
  14. distillationdistilled

출처 및 근거

ORD 기록
ord-297a6ac8e1db441b8c4c35901126cee7
출처 데이터셋
uspto-grants-1984_03
특허 번호
US04436939

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