Hexanal → 1-Octyn-3-ol

HRID 1776453Notes

Reaction equation

HRID 1776453 reaction equation
[CH:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C-]#[C-].[Na+].[Na+].[C:12]1(C)C(C)=CC=C[CH:17]=1>O1CCCC1>[CH:12]#[C:17][CH:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 6184HexanalHCID 7237O-XyleneHCID 178463197HCID 178463197, compound

Product 1

HCID 131661-Octyn-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 750-mL reactor is loaded with 40.1 g (400 mmoles) i.e. 49.2 mL of hexanal (RN 66-25-1) and 400 mL of anhydrous tetrahydrofuran and 100 g of a suspension of 18% sodium acetylide (RN 1066-26-8) in xylene (375 mmoles) is added by portions accompanied by stirring. An exothermic reaction takes place. Stirring is then continued for another 2 hours at no particular temperature. After hydrolysis, extractions and concentration, fractionation is carried out under reduced pressure.

Workup

  1. additionis added by portions
  2. customAn exothermic reaction
  3. stirringStirring
  4. customAfter hydrolysis, extractions and concentration, fractionation

Sources & evidence

ORD record
ord-85eb0e4a89c541f49692446b2719b5df
Source dataset
uspto-grants-2016_02
Patent number
US09265852B2

Reaction notes

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