Potassium Hydroxide → HCID 23049308, compound

HRID 1722219Notes

Reaction equation

HRID 1722219 reaction equation
[C:1]1([C:7]#[C:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[C:13]([O:15]CC)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>CO.O>[C:1]1([C:7]#[C:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 10656958HCID 10656958, compound

Product 1

HCID 23049308HCID 23049308, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 7-phenylhept-2E-en-6-ynoate (2.5 g) in methanol was added KOH (2.6 g) in water (6 ml). The mixture was stirred at 50° C. under a nitrogen atmosphere for 40 minutes, cooled, diluted with water (20 ml) and washed with ether (15 ml). The aqueous layer was acidified with 10% HCl and extracted with ether. The ether extracts were combined and dried over MgSO4, and the solvent was distilled off (adding dry benzene (4 ml) to form azeotrope with traces of water) to give 7-phenylhept-2E-en-6-ynoic acid (2 g) as a colourless oily solid.

Workup

  1. temperaturecooled
  2. washwashed with ether (15 ml)
  3. extractionextracted with ether
  4. dry with materialdried over MgSO4
  5. distillationthe solvent was distilled off
  6. addition(adding dry benzene (4 ml) to form azeotrope with traces of water)

Sources & evidence

ORD record
ord-025e0a7adfa04361ba9862272893340c
Source dataset
uspto-grants-1989_08
Patent number
US04855086

Reaction notes

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