Isobutanol → Furmecyclox

HRID 1733173Notes

Reaction equation

HRID 1733173 reaction equation
[CH:1]1([N:7]([O:14][CH3:15])[C:8](=[O:13])[CH2:9][C:10]([CH3:12])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O[CH:20]([CH3:23])[CH:21]=O)(=O)C.C(O)C(C)C>[Fe].O>[CH3:15][O:14][N:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:8]([C:9]1[CH:21]=[C:20]([CH3:23])[O:11][C:10]=1[CH3:12])=[O:13]

Participants

6

Reactant 3

HCID 6560IsobutanolHCID 907282-(Acetyloxy)propanalHCID 20300591HCID 20300591, compound

Product 1

HCID 43359Furmecyclox

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 85.2 parts of N-cyclohexyl-N-methoxyacetoacetamide and 58.2 parts of 95.7% pure α-acetoxypropionaldehyde is added dropwise to a suspension of 19.4 parts of iron-III chloride in 100 parts of isobutanol at 40°-45° C. The mixture is then kept at 45° C. for 7.5 hours. Water is added to the reaction mixture, the batch is extracted with methylene chloride and the extract is evaporated. 104 parts of crude product are obtained; this can be distilled at 138°-145° C./0.3 mm Hg, to give 88.5 parts of pure O-methyl-N-cyclohexyl-2,5-dimethylfuran-3-hydroxamic acid.

Workup

  1. extractionthe batch is extracted with methylene chloride
  2. customthe extract is evaporated
  3. custom104 parts of crude product are obtained
  4. distillationthis can be distilled at 138°-145° C./0.3 mm Hg

Sources & evidence

ORD record
ord-8cf8867a50cf4452bdeadc58a7da85c8
Source dataset
uspto-grants-1980_12
Patent number
US04240973

Reaction notes

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