Citric Acid → HCID 12723855, compound

HRID 1665923Notes

Reaction equation

HRID 1665923 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.C(O)(=O)C[C:12](CC(O)=O)(C(O)=O)[OH:13]>C(OC=O)C.C1COCC1.[Cl-].[Na+].O>[CH3:1][C:2]1([CH3:9])[CH2:7][CH:6]([CH:12]=[O:13])[C:5](=[O:8])[CH2:4][CH2:3]1

Participants

6

Reactant 2

HCID 311Citric AcidHCID 138166Cyclohexanone, 4,4-dimethyl-

Product 1

HCID 12723855HCID 12723855, compound

Reagents, catalysts & solvents 3

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

Procedure

To an ice-cold solution of K. tert.-butylate (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 it 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 poured 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-ebfb2aed123d45c6879c9c4fad8c0f13
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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