Hydrochloric Acid → 4-Propylhept-1-en-4-ol

HRID 466248

반응식

HRID 466248 반응식
[CH3:1][CH2:2][CH2:3][C:4](=[O:8])[CH2:5][CH2:6][CH3:7].[CH2:9]([Mg]Br)[CH:10]=[CH2:11].C(Br)C=C.[NH4+].[Cl-].Cl>C(OCC)C>[OH:8][C:4]([CH2:9][CH2:10][CH3:11])([CH2:5][CH2:6][CH3:7])[CH2:3][CH:2]=[CH2:1]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 312464-HeptanoneHCID 178455850HCID 178455850, 화합물

생성물 1

HCID 5513824-Propylhept-1-en-4-ol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

113 g of 4-heptanone in 1000 ml of dry diethyl ether was slowly added to a solution of allylmagnesium bromide, prepared from 36.5 g of Mg and 178 g of allyl bromide in 500 ml dry diethyl ether. After the addition the mixture was refluxed for 10 hrs. The reaction mixture was poured on a mixture of 150 g ice, 450 ml of 20% NH4Cl and 350 ml of 5M HCl. The ether phase was separated and the water phase extracted with diethyl ether (3×100 ml). The combined organic phases were then washed with a Na2CO3 -solution and water, dried with Na2SO4 and evaporated. The residue was distilled. Yield: 142 g (b.p. 38°-40° C./0.1 torr) 1H-NMR(CDCl3): δ0.9(6H,CH3), 1.3-1.6(9H,CH2,OH), 2.1-2.3 (CH2C=C), 5.0-5.2(CH2 =C), 5.6-6.1 (CH=C)

후처리

  1. additionAfter the addition the mixture
  2. temperaturewas refluxed for 10 hrs
  3. customThe ether phase was separated
  4. extractionthe water phase extracted with diethyl ether (3×100 ml)
  5. washThe combined organic phases were then washed with a Na2CO3 -solution and water
  6. dry with materialdried with Na2SO4
  7. customevaporated
  8. distillationThe residue was distilled

출처 및 근거

ORD 기록
ord-a3d205f1e1574d3a8469185ccbac3dce
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155220

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