Formaldehyde → 2-Nitrotoluene

HRID 1155209

Reaction equation

HRID 1155209 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])([O-:3])=[O:2].[CH2:11]=[O:12].[OH-:13].[K+].[CH3:15]N(C)C=O>O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:11]([OH:12])[CH3:15])([O-:2])=[O:13].[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 6228DimethylformamideHCID 69442-NitrotolueneHCID 14797Potassium Hydroxide

Product 2

HCID 69442-NitrotolueneHCID 978511-(2-Nitrophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 137 g (1 mole) of o-nitrotoluene, 120 g of paraformaldehyde, 34 g of potassium hydroxide and 500 ml of dimethyl formamide containing 0.7% by weight of water is stirred at 30° C. for 1.5 hours and then at 55° C. for 1 hour. The reaction mixture is processed as described in Example 1 to obtain 35 g of o-nitrophenylethanol, 20 g of o-nitrotoluene and 35 g of bis-methylol compounds. The bis-methylol compounds were identified by gas chromatographical mass spectrum (GCMS) analysis.

Workup

  1. waitat 55° C. for 1 hour

Sources & evidence

ORD record
ord-8656c1d09c184b4da34a03225db3f9b9
Source dataset
uspto-grants-1981_11
Patent number
US04299992

Linked notes

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