Methanol → 8-(2-Furyl)-8-methoxy-5-octynoic acid

HRID 1032500Notes

Reaction equation

HRID 1032500 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([O:17][CH3:18])[CH2:7][C:8]#[C:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14].[OH-].[K+].CO>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([O:17][CH3:18])[CH2:7][C:8]#[C:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 22166135Methyl 8-(2-furyl)-8-methoxy-5-octynoate

Product 1

HCID 221661348-(2-Furyl)-8-methoxy-5-octynoic acidYield 95.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.25 g of methyl 8-(2-furyl)-8-methoxy-5-octynoate, 0.66 g of 85% potassium hydroxide, 15 ml of methanol and 10 ml of water was heated under reflux for one hour. The methanol was evaporated and the residue partitioned with ether and water. The aqueous layer was chilled at 0° to 10° C., acidified with hydrochloric acid and the product extracted with ether. The extract was washed with brine, dried and concentrated, giving 1.13 g of the desired compound as a colorless oil. The identification is established by PMR; δ 3.35 (3H, s, methyl ether).

Workup

  1. temperatureunder reflux for one hour
  2. customThe methanol was evaporated
  3. customthe residue partitioned with ether and water
  4. temperatureThe aqueous layer was chilled at 0° to 10° C.
  5. extractionthe product extracted with ether
  6. washThe extract was washed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-768eafe3be2b41e6a9396fbf75057890
Source dataset
uspto-grants-1990_09
Patent number
US04958037

Reaction notes

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