Formaldehyde → 1-(4-Chlorophenyl)-2-butyn-1-ol

HRID 1789456

반응식

HRID 1789456 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5](CC#C)=[CH:4][CH:3]=1.[CH2:11]([Li])[CH2:12][CH2:13]C.[CH2:16]=[O:17].[Cl-:18].[Na+]>CCOCC.CCCCCC>[Cl:18][C:2]1[CH:7]=[CH:6][C:5]([CH:16]([OH:17])[C:11]#[C:12][CH3:13])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 712FormaldehydeHCID 5234Sodium ChlorideHCID 136602551-Chloro-4-(2-propyn-1-yl)benzeneHCID 178418339Butyllithium

생성물 1

HCID 201883391-(4-Chlorophenyl)-2-butyn-1-ol

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8058Hexane용매

실험 절차

Under nitrogen and with cooling, to a solution of 150.6 g (1.0 mole) 1-chloro-4-(2-propynyl)benzene in 600 ml of anhydrous ether, add dropwise 400 ml of 2.5M n-butyllithium (1.0 mole) in hexane. When addition is complete, stir a further 30 minutes and under N2 add 31 g of para-formaldehyde. Stir the mixture in a dry ice/acetone bath for 1 hour. Allow to warm to room temperature and then allow to reflux. When the reaction is complete, add 400 ml of saturated aqueous sodium chloride. Separate the layers and extract the aqueous layer with ether. Wash the combined ether solution, wash with water and dry over magnesium sulfate. Evaporate off the ether, dissolve the residue in hot cyclohexane which yielded crystalline material the title compound.

후처리

  1. additionWhen addition
  2. stirringStir the mixture in a dry ice/acetone bath for 1 hour
  3. temperatureto reflux
  4. customSeparate the layers
  5. extractionextract the aqueous layer with ether
  6. washWash the combined ether solution
  7. washwash with water
  8. dry with materialdry over magnesium sulfate
  9. customEvaporate off the ether
  10. dissolutiondissolve the residue in hot cyclohexane which

출처 및 근거

ORD 기록
ord-b179caa1edde4d7db85b74b59893ce31
출처 데이터셋
uspto-grants-1987_08
특허 번호
US04689341

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