Ethylene Oxide → 3-Octyn-1-ol

HRID 1065947Notes

Reaction equation

HRID 1065947 reaction equation
[CH2:1]1[O:3][CH2:2]1.[CH2:4]([C:8]#[CH:9])[CH2:5][CH2:6][CH3:7]>>[CH2:1]([OH:3])[CH2:2][C:7]#[C:6][CH2:5][CH2:4][CH2:8][CH3:9]

Participants

3

Reactant 2

HCID 6354Ethylene OxideHCID 127321-Hexyne

Product 1

HCID 846943-Octyn-1-ol

Procedure

Into the solution of the Grignard reagent obtained above and kept at 0° to 60° C., ethylene oxide is added dropwise preferably in an amount of 1.6 to 3 times by moles based on the starting butylacetylene and the reaction mixture is hydrolyzed by contacting with an aqueous acidic solution followed by distillation to give 3-octyn-1-ol (reaction (ii)). The yield is usually 80 to 85% of the theoretical value.

Workup

  1. customkept at 0° to 60° C.
  2. distillationfollowed by distillation

Sources & evidence

ORD record
ord-25e75fb571db434393eb31ed002727ae
Source dataset
uspto-grants-1982_05
Patent number
US04331820

Reaction notes

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