Tetrahydrofuran → 4-(4-Formylcyclohexyl)benzonitrile

HRID 653354

반응식

HRID 653354 반응식
C[O:2][CH:3]=[C:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.O1CCCC1>O>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([CH:7]2[CH2:8][CH2:9][CH:4]([CH:3]=[O:2])[CH2:5][CH2:6]2)=[CH:11][CH:12]=1)#[N:15]

참가 물질

4

반응물 2

HCID 8028TetrahydrofuranHCID 19739357p-[4-(Methoxymethylene)cyclohexyl]benzonitrile

생성물 1

HCID 117698294-(4-Formylcyclohexyl)benzonitrile수율 100%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 4.2 g of p-[4-(methoxymethylene)cyclohexyl]benzonitrile and 100 ml of tetrahydrofuran/2N hydrochloric acid (vol. 4:1) was heated to reflux for 30 minutes in a round flask. The mixture was subsequently poured into 100 ml of water and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed once with 100 ml of water, dried over magnesium sulphate and concentrated. There were obtained 3.9 g (100%) of 4-(p-cyanophenyl)cyclohexanecarboxaldehyde as a colourless oil which was used in the next step without further purification: trans/cis ratio about 3:1, Rf-value (ethyl acetate/petroleum vol. 3:7) 0.41. By recrystallization from hexane there could be obtained pure trans-4-(p-cyanophenyl)cyclohexanecarboxaldehyde; m.p. 57.1° C.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes in a round flask
  3. extractionextracted three times with 100 ml of diethyl ether each time
  4. washThe organic phases were washed once with 100 ml of water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-eddb7b5a620f411aad9f8f9596132082
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04676604

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