Acetylene → 1,1-Bis(2,4-dimethylphenyl)-2-propyn-1-ol

HRID 622268Notes

Reaction equation

HRID 622268 reaction equation
[CH:1]#[CH:2].C(=O)=O.CO.[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[CH3:25])=[O:17]>O1CCCC1>[CH3:25][C:19]1[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:18]=1[C:16]([C:10]1[CH:11]=[CH:12][C:13]([CH3:15])=[CH:14][C:9]=1[CH3:8])([OH:17])[C:1]#[CH:2]

Participants

5

Reactant 3

HCID 6326AcetyleneHCID 12274022Bis(2,4-dimethylphenyl)methanoneHCID 21973728Carbon dioxide methanol

Product 1

HCID 136285431,1-Bis(2,4-dimethylphenyl)-2-propyn-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.5 g of Fe(NO3)3.9H2O and 49 g of sodium are added to liquid ammonia (1.5 ) to produce sodium amide. Then acetylene gas is introduced into the reaction mixture at a temperature of -40° C. to -65° C. (whilst cooling using dry ice-methanol) for one hour while stirring. Then, an anhydrous tetrahydrofuran solution containing 476 g of di-(2,4-dimethylphenyl) ketone is added dropwise to the reaction mixture while cooling and stirring. After further stirring for 2 hours, the mixture is left at room temperature overnight. After removal of ammonia from the reaction solution by evaporation, 3N diluted HCl (300 ml) is added to the solution. After extraction with ether, the ether layer is washed with water and dried. After removal of ether by evaporation, 1,1-bis(2,4-dimethylphenyl)-2-propyn-1-ol is obtained as colourless oily product with a yield of 450 g.

Workup

  1. additionis added dropwise to the reaction mixture
  2. temperaturewhile cooling
  3. stirringstirring
  4. stirringAfter further stirring for 2 hours
  5. customAfter removal of ammonia from the reaction solution
  6. customby evaporation, 3N diluted HCl (300 ml)
  7. additionis added to the solution
  8. extractionAfter extraction with ether
  9. washthe ether layer is washed with water
  10. customdried
  11. customAfter removal of ether
  12. customby evaporation

Sources & evidence

ORD record
ord-2117a2f738cf463d88c9532d8264dea5
Source dataset
uspto-grants-1988_09
Patent number
US04769502

Reaction notes

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