Nitroethane → 4-Methyl-alpha-(1-nitroethyl)benzenemethanol

HRID 1731206Notes

Reaction equation

HRID 1731206 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.S(=O)(O)[O-].[Na+].[N+:15]([CH2:18][CH3:19])([O-:17])=[O:16].[OH-].[Na+]>O>[N+:15]([CH:18]([CH3:19])[CH:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:9])=[CH:2][CH:3]=1)[OH:8])([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 6587NitroethaneHCID 77254-MethylbenzaldehydeHCID 14798Sodium HydroxideHCID 23665763Sodium Bisulfite

Product 1

HCID 130961304-Methyl-alpha-(1-nitroethyl)benzenemethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure of Example 1 was followed for the reaction of 120 g of p-tolualdehyde and 114 g of sodium bisulfite with 150 g of 1-nitroethane and 80 g of sodium hydroxide. Water was the solvent. The final product was a yellow liquid weighing 103 g: ir (film) 2.85 (m), 3.4 (m), 6.5 (s), 7.2 (m), 7.35 (m), 9.5 (m), 12.15 (m) microns; nmr (CDCl3) 7.12 (4H, s), 5.0 to 4.5 (2H, m), 2.95 (1H, s), 2.3 (3H, s), 1.4 and 1.2 (3H, doublet and doublets) ppm.

Sources & evidence

ORD record
ord-eaf1036086284bed8e1faa298d394f92
Source dataset
uspto-grants-1976_11
Patent number
US03995063

Reaction notes

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