1-Hexanol → N1-(1-Methylethyl)-1,4-benzenediamine

HRID 3981

Reaction equation

HRID 3981 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]=O)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[OH-].[Na+].C(O)CCCCC>>[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 81031-HexanolHCID 14798Sodium HydroxideHCID 21909787N-isopropyl-4-nitrosoaniline

Product 1

HCID 85306N1-(1-Methylethyl)-1,4-benzenediamine

Procedure

Following essentially the procedure of Example 1, 66.0 g (0.25 mole) N-isopropyl-4-nitrosoaniline, 20 g (50%) sodium hydroxide and 264 g n-hexanol were kept at 100° C. for 1.5 hours. HPLC analysis of the reaction mixture indicated absence of the nitroso starting compound. By vacuum distillation (95°-101° C. at 13.3-26.6 Pa), 31.3 g of product were recovered (48.6 wt. % yield).

Workup

  1. distillationBy vacuum distillation (95°-101° C. at 13.3-26.6 Pa), 31.3 g of product
  2. customwere recovered
  3. custom(48.6 wt. % yield)

Sources & evidence

ORD record
ord-c383faf3f6174cd6aefc2d5b32c406fe
Source dataset
uspto-grants-1988_02
Patent number
US04723040

Linked notes

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