Hydrochloric Acid → 2,2-Diphenyl-2-(2-propynyl)acetaldehyde

HRID 1657272Notes

Reaction equation

HRID 1657272 reaction equation
[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:10][C:11]#[CH:12])[C:8]#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH2:25].Cl>O1CCCC1>[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:10][C:11]#[CH:12])[CH:8]=[O:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 108234172,2-Diphenylpent-4-ynenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 107997012,2-Diphenyl-2-(2-propynyl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,2-diphenyl-2-(2-propynyl)acetonitrile (1.38 g) and lithium aluminum hydride (0.21 g) in tetrahydrofuran (15 ml) was refluxed for 2 hours. The reaction mixture was poured into cold water, acidified with hydrochloric acid and extracted with diethyl ether. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of n-hexane and benzene (1:1) as an eluent to give 2,2-diphenyl-2-(2-propynyl)acetaldehyde (0.46 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel with a mixture of n-hexane and benzene (1:1) as an eluent

Sources & evidence

ORD record
ord-53da709d82214db89488facac587c2c3
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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