Methyl Isobutyl Ketone → HCID 19787426, compound

HRID 1657235Notes

Reaction equation

HRID 1657235 reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.[CH2:11]([C:15]([CH3:17])=O)[CH:12]([CH3:14])[CH3:13]>S(=O)(=O)(O)O>[CH3:17][C:15](=[N:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1)[CH2:11][CH:12]([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 7909Methyl Isobutyl KetoneHCID 1586545-Amino-2-chloro-4-fluorophenol

Product 1

HCID 19787426HCID 19787426, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
100 °C

Procedure

A 50-ml four-neck flask equipped with a Vigreux column (2 cmφ×25 cm) and a dehydrating column attached thereon was charged with 5-amino-2-chloro-4-fluorophenol (1.62 g), methyl isobutyl ketone (32.4 g) and concentrated sulfuric acid (50 mg). The mixture was dehydrated under reflux at 100° C. under reduced pressure (constant at 500 mmHg) for 7 hours. The concentration under reduced pressure gave 2.4 g of 5-(1,3-dimethylbutylidenamino)-2-chloro-4-fluorophenol (yield, 98%). It was found that the mass spectrum and NMR spectrum of the compound thus obtained correspond to those of the compound obtained in Example 1.

Workup

  1. customA 50-ml four-neck flask equipped with a Vigreux column (2 cmφ×25 cm)
  2. concentrationThe concentration under reduced pressure

Sources & evidence

ORD record
ord-9313bc23cebe40e7ae65dd7306baebbd
Source dataset
uspto-grants-1993_10
Patent number
US05256822

Reaction notes

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