Sulfuric Acid → N-[1,1-dimethyl-2-(2,4,6-trimethylphenyl)ethyl]formamide

HRID 966102Notes

Reaction equation

HRID 966102 reaction equation
[C-]#[N:2].[K+].S(=O)(=O)(O)O.[CH3:9][C:10](O)([CH3:21])[CH2:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[CH3:20].[C:23](=[O:26])([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[CH3:9][C:10]([NH:2][CH:23]=[O:26])([CH3:21])[CH2:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[CH3:20]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 10340Sodium CarbonateHCID 223145482-Methyl-1-(2,4,6-trimethylphenyl)propan-2-ol

Product 1

HCID 22314552N-[1,1-dimethyl-2-(2,4,6-trimethylphenyl)ethyl]formamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

90 mL of glacial acetic acid and 33 g of potassium cyanide are combined while cooling with ice. 90 mL of sulfuric acid and 90 mL of glacial acetic acid are then added dropwise at 20° C. 65 g of 2-methyl-1-(2,4,6-trimethylphenyl)propan-2-ol is slowly added to the solution at constant temperature. After the addition has ended, the mixture is stirred for a further hour. The mixture is poured onto ice water, neutralized with sodium carbonate solution, and extracted with diethyl ether. The solvent is distilled off under reduced pressure and the residue is fractionally distilled. Yield: 55 g (74%); bp0.1: 155° C.

Workup

  1. temperaturewhile cooling with ice
  2. additionAfter the addition
  3. additionThe mixture is poured onto ice water
  4. extractionextracted with diethyl ether
  5. distillationThe solvent is distilled off under reduced pressure
  6. distillationthe residue is fractionally distilled
  7. custom155° C.

Sources & evidence

ORD record
ord-68ba0bacb06145f1b0b9d0110ba4a991
Source dataset
uspto-grants-2005_10
Patent number
US06951888B2

Reaction notes

Loading…