Sodium Hydroxide → 478045-62-4

HRID 2085072Notes

Reaction equation

HRID 2085072 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:5])C.[OH-].[Na+]>CO>[CH:9]1([C@@H:7]2[CH2:8][C@H:6]2[C:4]([OH:5])=[O:3])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69553659HCID 69553659, compound

Product 1

HCID 18665782478045-62-4Yield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude ester (726 mg, 3.70 mmol, 1 equiv.) from above was dissolved in 20 mL MeOH and treated with 2.0 M aqueous NaOH solution (10 mL). The reaction mixture was stirred at room temperature for 3 h and then placed on a rotary evaporator to remove MeOH. Water was added and the mixture was washed once with ether. The aqueous layer was then acidified with 6 N HCl aqueous solution and the product was extracted with ether 3 times. The combined organics were washed once with brine, then dried (MgSO4). The solution was filtered through a small plug of SiO2 and the solvents removed in vacuo, providing 458 mg (2.72 mmol, 74%) of trans-2-cyclohexyl-cyclopropanecarboxylic acid.

Workup

  1. customplaced on a rotary evaporator
  2. customto remove MeOH
  3. additionWater was added
  4. washthe mixture was washed once with ether
  5. extractionthe product was extracted with ether 3 times
  6. washThe combined organics were washed once with brine
  7. dry with materialdried (MgSO4)
  8. filtrationThe solution was filtered through a small plug of SiO2
  9. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-44e367381b60413181be40e8f5129b9e
Source dataset
uspto-grants-2004_04
Patent number
US06720321B2

Reaction notes

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