Potassium Hydroxide → HCID 22166141, compound

HRID 1032501Notes

Reaction equation

HRID 1032501 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([OH:17])[CH2:7][C:8]#[C:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14].[OH-].[K+]>CO>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([OH:17])[CH2:7][C:8]#[C:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22166144HCID 22166144, compound

Product 1

HCID 22166141HCID 22166141, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4.73 g of methyl 8-(2-furyl)-8-hydroxy-5-octynoate in 60 ml of methanol was added 4 ml of 1 N potassium hydroxide. This mixture was stirred at reflux for one hour, then cooled and concentrated. The residue was partitioned between water and ether. The aqueous layer was separated, cooled to 0° C. and acidified with 1 N hydrochloric acid, then saturated with sodium chloride and extracted with ether. The ether extract was washed with brine, dried and concentrated, giving 4.39 g of the desired compound as an oil; PMR δ 4.85 (1H, t, CHOH).

Workup

  1. temperatureat reflux for one hour
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe residue was partitioned between water and ether
  5. customThe aqueous layer was separated
  6. extractionsaturated with sodium chloride and extracted with ether
  7. extractionThe ether extract
  8. washwas washed with brine
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f78c42d7b35144be949b6a3c633dd68c
Source dataset
uspto-grants-1990_09
Patent number
US04958037

Reaction notes

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