Sulfuric Acid → (E)-2-tridecen-4,7-diyn-1-ol

HRID 1106007Notes

Reaction equation

HRID 1106007 reaction equation
CC([O:6][CH2:7]/[CH:8]=[CH:9]/[C:10]#[C:11][CH2:12][C:13]#[C:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])OCC.S(=O)(=O)(O)O>CC(C)=O>[CH2:7]([OH:6])/[CH:8]=[CH:9]/[C:10]#[C:11][CH2:12][C:13]#[C:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 12821657(E)-4-methyl-3,5-dioxa-7-octadecen-9,12-diyne

Product 1

HCID 12821658(E)-2-tridecen-4,7-diyn-1-olYield 91.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of (E)-4-methyl-3,5-dioxa-7-octadecen-9,12-diyne(3.76 g) in acetone (60 mL) was treated with aqueous sulfuric acid (0.2 N, 6 mL) and left at room temperature for 3 hours. Half of the acetone was removed in vacuo and the residual solution was poured into water, extracted with ether and the combined extracts were dried (MgSO4), concentrated and purified by liquid chromatography (4:1 parts by volume hexane-ethyl acetate) to yield pure material (E)-2-tridecen-4,7-diyn-1-ol (2.5 g).

Workup

  1. customHalf of the acetone was removed in vacuo
  2. additionthe residual solution was poured into water
  3. extractionextracted with ether
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by liquid chromatography (4:1 parts by volume hexane-ethyl acetate)

Sources & evidence

ORD record
ord-847105c1692d455080369114984b6d46
Source dataset
uspto-grants-1982_01
Patent number
US04311645

Reaction notes

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