Sodium Hydroxide → HCID 178468167, compound

HRID 2059989Notes

Reaction equation

HRID 2059989 reaction equation
[CH2:1]([O:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([O:12]CC)=[O:11])[CH2:6][CH2:5]1)[CH3:2].[OH-].[Na+]>CO.C1COCC1>[CH2:1]([O:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178472491HCID 178472491, compound

Product 1

HCID 178468167HCID 178468167, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Cis/trans-Ethyl 4-(ethyloxy)cyclohexanecarboxylate (D2, 21 g, 105 mmol) was dissolved in MeOH-THF (100 mL-100 mL) and NaOH (5 eq., 0.5 mol, 40 mL, 12.5 N aqueous solution) was slowly added at room temperature. The mixture was stirred at room temperature overnight. The THF/MeOH was then evaporated and the crude was washed with Et2O. The aqueous phase was acidified and extracted with EtOAc (2×); organics were dried over Na2SO4, filtered and the solvent was evaporated to afford the title compound as a pale-yellow oil, 17.3 g, 96%.

Workup

  1. customThe THF/MeOH was then evaporated
  2. washthe crude was washed with Et2O
  3. extractionextracted with EtOAc (2×)
  4. dry with materialorganics were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-64c2774ecc0142f28637de8e33da58c5
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

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