Methane → 1-Octyn-3-ol

HRID 365160Notes

Reaction equation

HRID 365160 reaction equation
[CH:1]#[CH:2].C[Mg]Br.C.[CH:7](=[O:13])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH4+].[Cl-]>C1COCC1.CCOCC>[OH:13][CH:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:1]#[CH:2]

Participants

8

Reactant 5

HCID 297MethaneHCID 6184HexanalHCID 6326AcetyleneHCID 25517Ammonium ChlorideHCID 178418573HCID 178418573, compound

Product 1

HCID 131661-Octyn-3-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A rapid stream of acetylene was passed through a solution of 2M methyl magnesium bromide (100 ml) in THF until no more methane evolution was observed. 10 g of hexanal was added at 0° C., stirred for 1/2 h and a saturated solution of NH4Cl was added. The organic product was isolated by extraction with ether. The ether solution was washed with water, brine, dried over MgSO4 and evaporated to give a liquid, which was purified by distillation, to give 3-hydroxyoct-1-yne.

Workup

  1. washThe ether solution was washed with water, brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customto give a liquid, which
  5. distillationwas purified by distillation

Sources & evidence

ORD record
ord-67685600de43487a8ffd40a46957fa41
Source dataset
uspto-grants-1986_08
Patent number
US04608388

Reaction notes

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