2-Tolyl isocyanate → HCID 54075980, compound

HRID 2184999Notes

Reaction equation

HRID 2184999 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)([O-])=O.[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]=[C:20]=[O:21]>C(OC)(C)(C)C.[Pd]>[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][C:20](=[O:21])[NH:1][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 691942-Tolyl isocyanateHCID 692754-Nitrobenzyl alcohol

Product 1

HCID 54075980HCID 54075980, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 15413tert-Butyl methyl etherSolvent

Procedure

30.6 g (200 mmol) of 4-nitrobenzyl alcohol were hydrogenated with ice cooling over 1.0 g of palladium/carbon (10% strength; 50% water) in 500 ml of methyl tert-butyl ether. After the absorption of hydrogen was complete, the catalyst was filtered off and 24.8 ml (200 mmol) of 2-methylphenyl isocyanate were added to the filtrate at 15° C. with stirring in the course of 30 minutes. The precipitated solid was filtered off with suction and washed with methyl tert-butyl ether. Yield: 46.9 g (92%).

Workup

  1. customAfter the absorption of hydrogen
  2. filtrationthe catalyst was filtered off
  3. filtrationThe precipitated solid was filtered off with suction
  4. washwashed with methyl tert-butyl ether

Sources & evidence

ORD record
ord-1eee2a46a80d4f968e8eb4d2eeb78408
Source dataset
uspto-grants-2002_06
Patent number
US06399643B1

Reaction notes

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