Hexane → 112854-83-8

HRID 636071Notes

Reaction equation

HRID 636071 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[NH2:6].CC1(C)[O:18][C:17](=O)[CH:16]=[C:15]([CH3:20])[O:14]1.CCCCCC.C(OCC)(=O)C>C1(C)C(C)=CC=CC=1>[CH3:11][O:10][C:8]1[CH:7]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[CH:9]=1)[NH2:6].[CH3:11][O:10][C:8]1[CH:7]=[C:5]([NH:6][C:17](=[O:18])[CH2:16][C:15](=[O:14])[CH3:20])[CH:4]=[C:3]([O:2][CH3:1])[CH:9]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 663013,5-DimethoxyanilineHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

Product 2

HCID 663013,5-DimethoxyanilineHCID 256077112854-83-8Yield 186.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

A solution of 3,5-dimethoxy aniline 1 (5 g, 32.6 mmol) in xylene (20 mL) was taken in a 100 mL round bottom flask equipped with a reflux condenser and a dropping funnel and heated at 130° C. under nitrogen atmosphere. 2,2,6-trimethyl4H-1, 3-dioxin-4-one (4.64 g, 32.6 mmol) was then added dropwise for 25 min. Heating was continued at 125-130° C. for additional 3 h (TLC hexane : ethyl acetate, 6:4 Rf=0.3). The reaction mixture was cooled to 50° C. and xylene was removed under vacuum to get oily residue. The residue obtained was purified by column chromatography (silica gel hexane:ethyl acetate 4:1) to get product 1 N-(3,5-dimethoxyphenyl)-3-oxo-butanamide (9, 7.2 g) in 93% yield as an oily liquid.

Workup

  1. customequipped with a reflux condenser and a dropping funnel
  2. temperatureHeating
  3. temperatureThe reaction mixture was cooled to 50° C.
  4. customxylene was removed under vacuum
  5. customto get oily residue
  6. customThe residue obtained
  7. customwas purified by column chromatography (silica gel hexane:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-ad6cae087d924f819ef741bfc9345353
Source dataset
uspto-grants-2001_02
Patent number
US06191279B1

Reaction notes

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