Prop-1-yn-1-ol → 2,4-Hexadiyn-1,6-diol monophenylurethane

HRID 127344Notes

Reaction equation

HRID 127344 reaction equation
[C:1]([OH:4])#[C:2][CH3:3].[CH2:5]([OH:8])[C:6]#[CH:7].[C:9]1([NH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:5]([OH:8])[C:6]#[C:7][C:3]#[C:2][CH2:1][OH:4].[C:9]1([NH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 6432594Prop-1-yn-1-olHCID 867342142-Propyne-1-ol phenylurethane

Product 1

HCID 867342132,4-Hexadiyn-1,6-diol monophenylurethaneYield 78%

Procedure

The monomer 2,4-hexadiyn-1,6-diol-monophenylurethane is synthesized by the unsymmetrical coupling reaction of propyne-1-ol and 2-propyne-1-ol-phenylurethane and is purified by recrystallization of the crude product from ethyl acetate/petroleum ether. Recrystallization of a 0.4 gm sample from 100 ml of a 10:90 acetone/petroleum ether solvent mixture by slow evaporation at room temperature gives approximately 5 cm long needle-like crystals which turn pink upon exposure to light.

Workup

  1. customis purified by recrystallization of the crude product from ethyl acetate/petroleum ether
  2. customRecrystallization of a 0.4 gm sample from 100 ml of a 10:90 acetone/petroleum ether solvent mixture
  3. customby slow evaporation at room temperature
  4. customgives approximately 5 cm long needle-like crystals which

Sources & evidence

ORD record
ord-33a2f456fbf444e2a93a8c25e908765d
Source dataset
uspto-grants-1981_03
Patent number
US04255535

Reaction notes

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