HCID 11400871, compound → HCID 19373403, compound

HRID 1197370Notes

Reaction equation

HRID 1197370 reaction equation
[C:1]([O:9]CC)(=[O:8])/[CH:2]=[CH:3]/[CH2:4][CH2:5][C:6]#[CH:7]>CO>[C:1]([OH:9])(=[O:8])/[CH:2]=[CH:3]/[CH2:4][CH2:5][C:6]#[CH:7]

Participants

3

Reactant 1

HCID 11400871HCID 11400871, compound

Product 1

HCID 19373403HCID 19373403, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl (E)-hept-2-en-6-ynoate (1.8 g) in 50% aqueous methanol containing 5% sodium hydroxide was stirred at ambient temperature overnight. The methanol was removed under reduced pressure and the resulting aqueous phase was extracted with dichloromethane. The aqueous phase was adjusted to pH 1 with concentrated hydrochloric acid and re-extracted with dichloromethane. These organic extracts were washed with brine, dried over anhydrous magnesium sulphate and then evaporated in vacuo to leave (E)-hept-2-en-6-ynoic acid as a white solid (1.3 g).

Workup

  1. customThe methanol was removed under reduced pressure
  2. extractionthe resulting aqueous phase was extracted with dichloromethane
  3. extractionre-extracted with dichloromethane
  4. washThese organic extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-6cb5ef9e1f0a45ca8d9269d61be47535
Source dataset
uspto-grants-1992_05
Patent number
US05116862

Reaction notes

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