Diethyl Ether → HCID 15524044, compound

HRID 1422136Notes

Reaction equation

HRID 1422136 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]([CH3:18])[OH:17])=[N:2]1.C(OCC)C>N1C=CC=CC=1.[O-2].[O-2].[O-2].[Cr+6]>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16](=[O:17])[CH3:18])=[N:2]1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 15550300HCID 15550300, compound

Product 1

HCID 15524044HCID 15524044, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 1049PyridineSolvent

Procedure

In 46 ml of dry pyridine was dissolved 4.6 g of 2-(1,2-benzisoxazol-3-yl)-α-methyl-benzenemethanol. Under an atmosphere of nitrogen, 4.6 g of chromium trioxide was slowly added at room temperature. After stirring at room temperature for 4 h, 200 ml of diethyl ether were added to the reaction mixture. The precipitates were filtered off and washed with diethyl ether. The filtrate was washed with 5 portions of 100 ml of 2N aqueous hydrochloric acid and 2 portions of 200 ml of water, dried over magnesium sulphate and evaporated to dryness to afford 4.5 g of 1-[2-(1,2-benzisoxazol-3-yl)phenyl]-ethanone, melting at 108° C.

Workup

  1. filtrationThe precipitates were filtered off
  2. washwashed with diethyl ether
  3. washThe filtrate was washed with 5 portions of 100 ml of 2N aqueous hydrochloric acid and 2 portions of 200 ml of water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-c207a39eff0f416687bdcde0535fdae9
Source dataset
uspto-grants-2000_06
Patent number
US06080773

Reaction notes

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