Cyclohexanone → (1-Hydroxycyclohexyl)(4-methoxyphenyl)acetonitrile

HRID 64981

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HRID 64981 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.C([Li])CCC.CCCCCC.[C:23]1(=[O:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[Cl-].[NH4+]>O1CCCC1>[C:10]([CH:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:23]1([OH:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)#[N:11]

참가 물질

7

반응물 5

HCID 7967CyclohexanoneHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 66031Benzeneacetonitrile, 4-methoxy-HCID 178418339Butyllithium

생성물 1

HCID 9899621(1-Hydroxycyclohexyl)(4-methoxyphenyl)acetonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-70 °C

실험 절차

p-Methoxyphenylacetonitrile (50 gm, 0.3 mole) was added to dry tetrahydrofuran (250 ml) and the solution cooled to -70° C. under nitrogen. n-Butyl lithium in hexane (210 ml, 0.3 mole) was added dropwise, with stirring. The temperature was maintained below -50° C. and a yellow precipitate appeared. After the addition was complete, the reaction mixture was maintained below -50° C. for 30 minutes and cyclohexanone (35 ml, 0.3 mole) was added. After a further 45 minutes below -50° C. the temperature was allowed to rise to 0° C. and a saturated ammonium chloride solution was added. The layers were separated and the aqueous layer extracted with diethyl ether. The combined organic solution was washed with brine, dried over magnesium sulphate and evaporated. The product crystallized (25.2 gm, m.p. 125°-127° C.).

후처리

  1. temperatureThe temperature was maintained below -50° C.
  2. additionAfter the addition
  3. temperaturethe reaction mixture was maintained below -50° C. for 30 minutes
  4. customto rise to 0° C.
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted with diethyl ether
  7. washThe combined organic solution was washed with brine
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. customThe product crystallized (25.2 gm, m.p. 125°-127° C.)

출처 및 근거

ORD 기록
ord-53b0532ff7824926866cd13eab492272
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04611078

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