Sodium amide → 4-amino-3,5-dimethylbenzaldehyde

HRID 462557Notes

Reaction equation

HRID 462557 reaction equation
[NH2:1][C:2]1[C:14]([CH3:15])=[CH:13][C:5]([CH:6]([OH:12])CS(C)(=O)=O)=[CH:4][C:3]=1[CH3:16].[NH2-].[Na+]>CS(C)=O>[NH2:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]([CH:6]=[O:12])=[CH:13][C:14]=1[CH3:15]

Participants

4

Reactant 2

HCID 24533Sodium amideHCID 538208514-Amino-3,5-dimethyl-alpha-[(methylsulfonyl)-methyl]-benzyl alcohol

Product 1

HCID 100347774-amino-3,5-dimethylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 14.6 g. of 4-amino-3,5-dimethyl-α-[(methylsulfonyl)-methyl]-benzyl alcohol in 50 ml. of absolute dimethylsulfoxide was treated with 1.17 g. of sodium amide, stirred for 2 hours at room temperature, diluted with 500 ml. of water and extracted with two 500 ml. portions of ethyl acetate. The ethyl acetate extract was washed with two 200 ml. portions of water and evaporated under vacuum. After recrystallization of the residue from cyclohexane, there was obtained 4-amino-3,5-dimethyl-benzaldehyde having a melting point of 75°-76° C.

Workup

  1. additiondiluted with 500 ml
  2. extractionof water and extracted with two 500 ml
  3. extractionThe ethyl acetate extract
  4. washwas washed with two 200 ml
  5. customportions of water and evaporated under vacuum
  6. customAfter recrystallization of the residue from cyclohexane

Sources & evidence

ORD record
ord-108e6ab545a343b5b07e1a58cbf918c3
Source dataset
uspto-grants-1985_05
Patent number
US04515948

Reaction notes

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