p-Toluenesulfonic acid → 3-(1,1-Dimethoxyethyl)hept-5-yn-2-one

HRID 437899Notes

Reaction equation

HRID 437899 reaction equation
[C:1]([CH:4]([CH2:8][C:9]#[C:10][CH3:11])[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].[CH3:12][O:13]C(OC)(C)C.[C:19]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:19][O:7][C:5]([O:13][CH3:12])([CH:4]([C:1](=[O:3])[CH3:2])[CH2:8][C:9]#[C:10][CH3:11])[CH3:6]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 203721333-(But-2-yn-1-yl)pentane-2,4-dione

Product 1

HCID 203721323-(1,1-Dimethoxyethyl)hept-5-yn-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 38.0 g. (0.25 mol.) of 3-acetyl-5-heptyn-2-one, 32.3 g. (0.31 mol.) of 2,2-dimethoxy-propane, and 5 mg. of p-toluenesulfonic acid in 25 ml. of absolute methanol and 25 ml. of benzene was slowly distilled until the material boiling below 65° had been removed, then stirred with 1 g. of sodium carbonate and filtered to produce 2,2-dimethoxy-3-acetyl-5-heptyne in the filtrate.

Workup

  1. distillationof benzene was slowly distilled until the material
  2. customboiling below 65°
  3. customhad been removed
  4. filtrationof sodium carbonate and filtered

Sources & evidence

ORD record
ord-776fb5b9af60495a8200cd3065b9a001
Source dataset
uspto-grants-1977_06
Patent number
US04032577

Reaction notes

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