Diethyl Ether → 4-Ethynylheptan-4-ol

HRID 1439012Notes

Reaction equation

HRID 1439012 reaction equation
C#C.[Na].[CH2:4]([C:7]([CH2:9][CH2:10][CH3:11])=[O:8])[CH2:5][CH3:6].[CH3:12][CH2:13]OCC>N>[CH2:4]([C:7]([CH2:9][CH2:10][CH3:11])([OH:8])[C:12]#[CH:13])[CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 6326Acetylene2×HCID 312464-HeptanoneHCID 5360545Sodium

Product 1

HCID 123838984-Ethynylheptan-4-ol

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To the acetylene solution in ammonia were added 23 g of finely divided sodium. The bubbling of acetylene was maintained for 1 hour after the introduction of the sodium. After that, 114 g (1 mol) of di-n-propyl ketone were added and the acetylene flow was maintained for 1 hour after which 500 ml of ether were added and the mixture was allowed to stand for 12 hours at room-temperature. It was then hydrolysed by adding damp ether followed by crushed ice. After acidification with 10% sulphuric acid, the ethereal phase was separated out, dried over magnesium sulphate and concentrated under reduced pressure.

Workup

  1. customThe bubbling of acetylene
  2. temperaturewas maintained for 1 hour after the introduction of the sodium
  3. additionwere added
  4. customby crushed ice
  5. customAfter acidification with 10% sulphuric acid, the ethereal phase was separated out
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-86c57f2fed414abab11804b20c45168e
Source dataset
uspto-grants-1977_11
Patent number
US04057644

Reaction notes

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