Potassium Hydroxide → 7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

HRID 1684527Notes

Reaction equation

HRID 1684527 reaction equation
[CH:1]12[O:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]([O:10]CC)=[O:9].[OH-].[K+]>O.C(O)C>[CH:1]12[O:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 12914722Ethyl 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate

Product 1

HCID 31593757-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3.0 g (17.8 mmol) of ethyl 7-oxabicyclo[2.2.1]hept-5-en-2-carboxylate are suspended in 10 ml of water and 20 ml of ethanol. The temperature is kept below 20° C. by cooling with ice, while 3.5 g (62.3 mmol) of potassium hydroxide are added. The mixture is stirred for 2 hours at ambient temperature, the ethanol is distilled off at a bath temperature of 30° C. and the aqueous solution is extracted with ethyl acetate. The aqueous phase is acidified to a pH of 6 while cooling with ice and shaken with dichloromethane, then the combined organic extracts are dried and evaporated down. 0.8 g (32% of theory) of the title compound are obtained as a brown oil.

Workup

  1. customis kept below 20° C.
  2. additionare added
  3. distillationthe ethanol is distilled off at a bath temperature of 30° C.
  4. extractionthe aqueous solution is extracted with ethyl acetate
  5. temperaturewhile cooling with ice
  6. stirringshaken with dichloromethane
  7. customthe combined organic extracts are dried
  8. customevaporated down

Sources & evidence

ORD record
ord-b635dd3125de4cb2995c963161e3dd0e
Source dataset
uspto-grants-1997_06
Patent number
US05641784

Reaction notes

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