Ethanol → 5-Heptynoic acid, 7-hydroxy-

HRID 971934Notes

Reaction equation

HRID 971934 reaction equation
S(=O)(=O)(O)O.[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12]CC#CCCCCl.[C-]#N.[K+].[OH-].[K+].[CH2:25]([OH:27])[CH3:26]>O>[OH:27][CH2:25][C:26]#[C:11][CH2:10][CH2:9][CH2:8][C:7]([OH:12])=[O:6]

Participants

7

Reactant 5

HCID 702EthanolHCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 14797Potassium HydroxideHCID 13779396HCID 13779396, compound

Product 1

HCID 53128155-Heptynoic acid, 7-hydroxy-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

By following the procedure of A. I. Rachlin, et al., cited above, 6-chloro-2-hexyn-1-ol is prepared by condensing propargyl alcohol tetrahydropyran-2-yl ether and the dihaloalkane of formula VIII, 1-bromo-3-chloropropane, to give 1-[(tetrahydropyran-2-yl)oxy]-6-chloro-2-hexyne, which is then converted to the desired compound followed by hydrolysis in the presence of sulfuric acid. The 6-chloro-2-hexyn-1-ol (280 g) is dissolved in ethanol (2.8 l) then water (560 ml) and potassium cyanide (290 g) is added and the mixture stirred and refluxed for 20 hr. Potassium hydroxide (768 g) and water (500 ml) are added and the stirred mixture kept at reflux for an additional 20 hr. Methanol is evaporated and the water phase is acidified with concentrated HCl and extracted with ether for 2 days in a continuous liquid-liquid extractor. The ether extract is dried (Na2SO4) and concentrated to give the title compound, nmr (CDCl3) δ 4.22 (m, 2 H), 7.41 (broad, 2H).

Workup

  1. temperaturerefluxed for 20 hr
  2. temperatureat reflux for an additional 20 hr
  3. customMethanol is evaporated
  4. extractionextracted with ether for 2 days in a continuous liquid-liquid extractor
  5. extractionThe ether extract
  6. dry with materialis dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5862007218bf4d25a640017cd5e96055
Source dataset
uspto-grants-1979_07
Patent number
US04161608

Reaction notes

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