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

HRID 65234

Reaction equation

HRID 65234 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-20fd872bfe264e6fb36a86a1a04070a7
Source dataset
uspto-grants-1986_09
Patent number
US04613609

Linked notes

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