Sodium Hydroxide → α-Methyl-α-2-propyn-1-ylbenzenemethanol

HRID 256733Notes

Reaction equation

HRID 256733 reaction equation
Cl[C:2]([CH2:4][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([OH:7])[CH3:6])=[CH2:3].[OH-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:8]1([C:5]([OH:7])([CH3:6])[CH2:4][C:2]#[CH:3])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22404520HCID 22404520, compound

Product 1

HCID 569355α-Methyl-α-2-propyn-1-ylbenzenemethanol

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

20.00 Grams of the 2-chloro-4-phenyl-1-penten-4-ol were dissolved in 50 g of toluene, and 30.5 g of a 40% sodium hydroxide aqueous solution and 65.57 g of tetra-n-butylammonium bromide were added. The mixture was allowed to react at 50° C. for 30 hours, and then was subjected to separation. The organic phase was washed with water, and the toluene was distilled off under reduced pressure. The resultant oily substance was purified by silica gel column chromatography to give 11.37 g of 4-phenyl-1-pentyn-4-ol; nD21 =1.537 FI-MS m/e 160(M+) (Propargyl compound/allene compound 100.0/0.0).

Workup

  1. customto react at 50° C. for 30 hours
  2. customwas subjected to separation
  3. washThe organic phase was washed with water
  4. distillationthe toluene was distilled off under reduced pressure
  5. customThe resultant oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b598667bd9bc4ab2bf7104f9ce6af5b3
Source dataset
uspto-grants-1993_11
Patent number
US05258529

Reaction notes

Loading…