Sodium Thiosulfate → Methyl 4-formylcyclohexane-1-carboxylate

HRID 1965079Notes

Reaction equation

HRID 1965079 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1.C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.CCOCC>[CH:2]([CH:3]1[CH2:4][CH2:5][CH:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:8]1)=[O:1]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate2×HCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester2×

Product 1

HCID 11252253Methyl 4-formylcyclohexane-1-carboxylateYield 99.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(hydroxymethyl)cyclohexanecarboxylate (Intermediate 87, 4.08 g, 23.7 mmol) in DCM was added NaHCO3 (9.95 g, 118 mmol), followed by Dess-Martin Periodinane (12.1 g, 28.4 mmol). The mixture was stirred at r.t. for 2.5 h. Et2O (60 mL) was added followed by an aq. solution of NaHCO3 (1 M, 60 mL) and a 20% aq. solution of sodium thiosulfate (40 mL). The resulting mixture was stirred overnight. The phases were separated and the aqueous phase was extracted with Et2O. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated in vacuo to yield the title compound (4.0 g, 99% yield): MS (EI) m/z 170 M+.

Workup

  1. stirringThe resulting mixture was stirred overnight
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with Et2O
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ab3ebf0e18ca4fa8aba98b38f3b4af70
Source dataset
uspto-grants-2013_04
Patent number
US08415483B2

Reaction notes

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