Oxalic Acid → HCID 12773962, compound

HRID 848619Notes

Reaction equation

HRID 848619 reaction equation
O1CCCCC1[O:7][CH2:8][C:9]#[C:10][CH2:11]/[CH:12]=[CH:13]/[CH2:14][CH2:15][CH3:16].C(O)(=O)C(O)=O>CO>[CH2:8]([OH:7])[C:9]#[C:10][CH2:11]/[CH:12]=[CH:13]/[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 12773961HCID 12773961, compound

Product 1

HCID 12773962HCID 12773962, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(2-tetrahydropyranyloxy)-trans-5-nonen-2-yne (61.5 g) in methanol (250 ml) was added 4% oxalic acid (250 ml). The reaction mixture was refluxed for 2 hours and concentrated under reduced pressure to give a residue, which was extracted with ether, washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give a yellowish oily residue. The oily residue was distilled under reduced pressure to give colorless oily trans-5-nonen-2-yne-1-ol (37 g).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. concentrationconcentrated under reduced pressure
  3. customto give a residue, which
  4. extractionwas extracted with ether
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a yellowish oily residue
  9. distillationThe oily residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-eedc9e2a0c75415689799839c63b7a25
Source dataset
uspto-grants-1981_10
Patent number
US04297096

Reaction notes

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