Sulfuric Acid → 1-(1,2-Benzoxazol-3-yl)ethan-1-one

HRID 1957528Notes

Reaction equation

HRID 1957528 reaction equation
S(=O)(=O)(O)O.[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8]([CH:15]([OH:17])[CH3:16])=[N:7]1>O.C(OCC)C>[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8]([C:15](=[O:17])[CH3:16])=[N:7]1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 19068200HCID 19068200, compound

Product 1

HCID 127064081-(1,2-Benzoxazol-3-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1.1 g of sodium bichromate dihydrate and 0.8 ml of sulfuric acid in 5 ml of water is slowly added dropwise to 1.6 g of 1-(1,2-benzisoxazol-3-yl)ethanol in 5 ml of diethyl ether. This mixture is stirred for 1 hour at room temperatur and then, with ice cooling, 50 ml of water are added and extraction wth diethyl ether is carried out three times. The combined ethereal extracts are washed once with a saturated solution of sodium bicarbonate, once with water and finally once with a saturated solution of sodium chloride, dried over sodium sulfate and concentrated under vacuum. The crude product is purified by chromatography over silica gel with ethyl acetate/hexane (1:3), giving 1-(1,2-benzisoxazol-3-yl)ethanone having a melting point of 30°-32° C.

Workup

  1. extractionextraction wth diethyl ether
  2. washThe combined ethereal extracts are washed once with a saturated solution of sodium bicarbonate, once with water and finally once with a saturated solution of sodium chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude product is purified by chromatography over silica gel with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-1105ea2b67ad44518eda1929a1b81baf
Source dataset
uspto-grants-1998_07
Patent number
US05786374

Reaction notes

Loading…