Sulfuric Acid → [5-(4-chlorophenyl)-1,3-oxazol-2-yl]methanol

HRID 623215Notes

Reaction equation

HRID 623215 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][C:16]([CH2:18][O:19]CC)=[N:15][CH:14]=2)=[CH:9][CH:8]=1>O>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[O:17][C:16]([CH2:18][OH:19])=[N:15][CH:14]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 21290694HCID 21290694, compound

Product 1

HCID 21290727[5-(4-chlorophenyl)-1,3-oxazol-2-yl]methanolYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

7.5 ml of concentrated sulphuric acid were added carefully to a suspension, cooled in ice, of 1.4 g (5.9 mmol) of 5-(4-chlorophenyl)-2-ethoxymethyl-oxazole in 4.5 ml of water. The resulting solution was stirred and heated at 140° C. under reflux for 4 hours, then cooled and poured on to 140 ml of ice/water. The mixture was extracted three times with 30 ml of dichloromethane each time. The combined dichloromethane extracts were washed with 50 ml of saturated sodium hydrogen carbonate solution, dried over sodium sulphate, filtered and evaporated. Recrystallization of the product from toluene yielded 0.80 g (65%) of 5-(4-chlorophenyl)-2-oxazolemethanol of melting point 100°-103.5° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperaturecooled
  3. extractionThe mixture was extracted three times with 30 ml of dichloromethane each time
  4. washThe combined dichloromethane extracts were washed with 50 ml of saturated sodium hydrogen carbonate solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customRecrystallization of the product from toluene

Sources & evidence

ORD record
ord-e3bcf4a429974b9486509ce358a43e74
Source dataset
uspto-grants-1988_09
Patent number
US04774253

Reaction notes

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