Toluene → 1-Pentyn-3-ol, 3-methyl-1-phenyl-

HRID 2296240Notes

Reaction equation

HRID 2296240 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].C1(C)C=CC=CC=1.[CH3:18][C:19](=[O:22])[CH2:20][CH3:21]>O>[CH3:18][C:19]([OH:22])([CH2:20][CH3:21])[C:8]#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6569Methyl Ethyl KetoneHCID 10821PhenylacetyleneHCID 14797Potassium Hydroxide

Product 1

HCID 1027291-Pentyn-3-ol, 3-methyl-1-phenyl-Yield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phenylacetylene (500 g, 4.2 mol) was added to a mixture of potassium hydroxide flake (290 g) and toluene (3 L). 2-Butanone (425 g, 5.9 mol) was added over 45 minutes keeping the temperature below 30° C. with periodic cooling and the resulting mixture agitated for 20 h at room temperature. Water (1 L) was added, the toluene solution washed until neutral, the solvent evaporated, and the residue distilled to give 517 g (71% yield) of 3-methyl-1-phenyl-1-pentyn-3-ol; bp 107°-110° C./3 mm; IR (film) 3400, 1150, 1000, 920 cm-1 ; NMR (CDCl3) 1.1 (3H, t), 1.6 (3H, s), 1.8 (2H, q), 2.2 (1H, s), 7.2-7.6 (5.H, m) δ; MS (m/e) 174, 156, 145, 43.

Workup

  1. customthe temperature below 30° C.
  2. temperaturewith periodic cooling
  3. washthe toluene solution washed until neutral, the solvent
  4. customevaporated
  5. distillationthe residue distilled

Sources & evidence

ORD record
ord-b3795c8b89fc4863a84ef13db61e0a2e
Source dataset
uspto-grants-1984_01
Patent number
US04428870

Reaction notes

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