Dimethyl Sulfoxide → 4-Aminobenzaldehyde

HRID 1680552Notes

Reaction equation

HRID 1680552 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1)([O-])=O.CS(C)=[O:13]>CN(C)C=O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:13])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 74734-Nitrotoluene

Product 1

HCID 111584-Aminobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure of Example 1 was followed except that 3.2 g (4.8% by weight of the p-nitrotoluene) of dimethylsulfoxide were substituted for the N,N-dimethylformamide, to obtain 38.3 g (0.317 mol) of p-aminobenzaldehyde and then 39.1 g (0.320 mol) of p-hydroxybenzaldehyde. Thus, the yield of the p-hydroxybenzaldehyde was 65.8%, based on the weight of p-nitrotoluene used.

Sources & evidence

ORD record
ord-03c3fd32e4044bfcaad27b68206f5f02
Source dataset
uspto-grants-1981_06
Patent number
US04273941

Reaction notes

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