Formaldehyde → HCID 11701082, compound

HRID 1504799Notes

Reaction equation

HRID 1504799 reaction equation
[C-:1]#[N:2].[K+].C=O.[C:6]([O:13][C:14](OC(C)(C)C)=O)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>CO>[C:6](=[O:7])([O:13][CH2:14][C:1]#[N:2])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 9032Potassium CyanideHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 11701082HCID 11701082, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of potassium cyanide (600 g, 9.22 mol) in methanol (10 L) was added formaldehyde (38% solution in water, 1457 g, 18 mol) dropwise at 0° C. After 1 hour, di-tert-butyl dicarbonate (3018 g, 13.83 mol) was added batchwise at 0° C. The reaction mixture was allowed to warm to ambient temperature. After 4 hours, the reaction mixture was quenched with water (2 L) and extracted with ethyl acetate (4×2 L). The organics were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford tert-butyl cyanomethyl carbonate. The product was used without further purification.

Workup

  1. waitAfter 4 hours
  2. customthe reaction mixture was quenched with water (2 L)
  3. extractionextracted with ethyl acetate (4×2 L)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c35c506567540fd832c898098dd0f2e
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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