Benzilic acid → 1-Butynyl alpha-phenyl-alpha-(1-butynyloxy)phenylacetate

HRID 918304

Reaction equation

HRID 918304 reaction equation
[C:1]1([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([OH:11])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](Br)#[C:19][CH2:20][CH3:21]>CN(C)C=O>[C:1]1([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([O:11][C:2]#[C:1][CH2:6][CH3:5])[C:8]([O:10][C:18]#[C:19][CH2:20][CH3:21])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6463Benzilic acidHCID 109970821-bromobut-1-yne

Product 1

HCID 215219091-Butynyl alpha-phenyl-alpha-(1-butynyloxy)phenylacetateYield 122.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Into a suspension of 1.5 g of 66% sodium hydride-paraffin in 20 cc of dimethylformamide was added a solution of 4.5 g of α-phenyl-α-hydroxyphenylacetic acid in 10 cc of dimethylformamide under cooling, and the mixture was stirred for 1 hour. Successively, 5.8 g of butynyl bromide was added thereto and the stirring was continued for 1 hour. The reaction mixture was poured in ice-water, and the resultant was subjected to extraction with ether. The ether extract was washed with an aqueous solution saturated with sodium chloride, and dried over sodium sulfate. Thereafter ether was distilled out and paraffin was removed to obtain 4.0 g of oily 1-butynyl α-phenyl-α-(1-butynyloxy)phenylacetate, nD25 1.5581.

Workup

  1. temperatureunder cooling
  2. waitthe stirring was continued for 1 hour
  3. extractionthe resultant was subjected to extraction with ether
  4. extractionThe ether extract
  5. washwas washed with an aqueous solution saturated with sodium chloride
  6. dry with materialdried over sodium sulfate
  7. distillationThereafter ether was distilled out and paraffin
  8. customwas removed

Sources & evidence

ORD record
ord-f80841a2d4694390a773a92664bc89e6
Source dataset
uspto-grants-1976_07
Patent number
US03970703

Linked notes

Loading…