Formaldehyde → 1-(Hydroxymethyl)-cyclohexanecarboxaldehyde

HRID 2229506Notes

Reaction equation

HRID 2229506 reaction equation
[CH:1]1([CH:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:9]=[O:10].[OH-].[Na+]>CO>[OH:8][CH2:7][C:1]1([CH:9]=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 16275Cyclohexanecarboxaldehyde

Product 1

HCID 131063971-(Hydroxymethyl)-cyclohexanecarboxaldehydeYield 59.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cold (0° C.) mixture of 100 g (0.891 mole) of cyclohexanecarboxaldehyde, 76.5 g of 37% of formaldehyde in 225 ml of methanol was added dropwise 90 ml of 1 N Sodium hydroxide in 1 h. The reaction mixture was stirred at room temperature over 48 then was evaporated to remove methanol. The reaction mixture was diluted with water and extracted with methylene chloride. The organic layer was washed with water, brine, and dried over sodium sulfate and concentrated under vacuum to give 75 g (59.7%) of thick oil. Proton NMR and mass spectra were consistent with the product.

Workup

  1. customthen was evaporated
  2. customto remove methanol
  3. additionThe reaction mixture was diluted with water
  4. extractionextracted with methylene chloride
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e38dab0bb5e74f7c89ad4fbda3396dc6
Source dataset
uspto-grants-2002_07
Patent number
US06420417B1

Reaction notes

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