Citric Acid → HCID 12723855, compound

HRID 1924809Notes

Reaction equation

HRID 1924809 reaction equation
C[C:2]([O-:5])(C)C.[K+].[CH3:7][C:8]1([CH3:15])[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.C(OC=O)C.[Cl-].[Na+].O>[CH3:7][C:8]1([CH3:15])[CH2:13][CH:12]([CH:2]=[O:5])[C:11](=[O:14])[CH2:10][CH2:9]1

Participants

7

Reactant 3

HCID 311Citric AcidHCID 138166Cyclohexanone, 4,4-dimethyl-HCID 23665647Potassium tert-butoxide

Product 1

HCID 12723855HCID 12723855, compoundYield 309.4%

Reagents, catalysts & solvents 3

HCID 8025Ethyl formateSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To an ice-cold solution of KOtBu (24.5 g, 109 mmol, 50% solution in tert.-butanol) in THF (700 mL), ethylformate (120 mL, 123 mmol) is slowly added. The mixture is stirred at rt for 30 min before a solution of 4,4-dimethyl-cyclohexanone (50 g, 396 mmol) in ethylformate (50 mL) and THF (70 mL) is added over a period of 20 min. Upon complete addition, stirring is continued at 15-20° C. for 30 min. The orange suspension is pourred onto 10% aq. citric acid solution (200 mL) and brine (200 mL) and extracted with EA (2×200 mL). The organic extracts are washed with 0.2 N aq. NaOH and brine, dried over Na2SO4 and evaporated to dryness to give 5,5-dimethyl-2-oxo-cyclohexanecarbaldehyde (52 g) as a yellow oil; LC-MS: tR=0.89 min, [M+1+CH3CN]+=196.15.

Workup

  1. additionis added over a period of 20 min
  2. additionUpon complete addition
  3. extractionextracted with EA (2×200 mL)
  4. washThe organic extracts are washed with 0.2 N aq. NaOH and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a7d0ecb58fa6450ba9c0e58abdc89e44
Source dataset
uspto-grants-2012_05
Patent number
US08178562B2

Reaction notes

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