Sodium Hydroxide → 2-Cyclohexylideneacetic acid

HRID 1638500Notes

Reaction equation

HRID 1638500 reaction equation
[C:1]1(=[CH:7][C:8]([O:10]CC)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[C:1]1(=[CH:7][C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 73776Ethyl cyclohexylideneacetate

Product 1

HCID 962062-Cyclohexylideneacetic acidYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The ethyl ester from (a) (343 mg, 2.04 mmol) was dissolved in ethanol (5 ml). A 5M aqueous solution of sodium hydroxide (0.82 ml, 4.04 mmol) was added. The solution was stirred at reflux for 3h whereupon a precipitate was formed, and all starting material had disappeared as indicated by tlc. After cooling, the ethanol was removed by evaporation and water (10 ml) was added. The basic solution was extracted with dichloromethane (10 ml) which was discarded. The aqueous layer was acidified with 2M hydrochloric acid and then extracted with ethyl acetate (2×10 ml). The organic layer was dried, filtered and evaporated to leave the title compound (b) (206 mg, 72%) as a sweet-smelling white solid, m.p. 84°-5° C. from ethanol and diethylether.

Workup

  1. customwas formed
  2. temperatureAfter cooling
  3. customthe ethanol was removed by evaporation and water (10 ml)
  4. additionwas added
  5. extractionThe basic solution was extracted with dichloromethane (10 ml) which
  6. extractionextracted with ethyl acetate (2×10 ml)
  7. customThe organic layer was dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-dccc3ea5c5e54934b0c225e9ba09eaa1
Source dataset
uspto-grants-1989_11
Patent number
US04880776

Reaction notes

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