Water → 2-Methyl-1,3-benzoxazol-6-ol

HRID 1271827Notes

Reaction equation

HRID 1271827 reaction equation
ON=C[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[OH:11].P(Cl)(Cl)(Cl)=O.O.[C:18]([O-])(=O)[CH3:19].[Na+].C[N:24](C=O)C>C(#N)C>[CH3:19][C:18]1[O:11][C:5]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:4]=2[N:24]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 94842Benzaldehyde, 2,4-dihydroxy-, oximeHCID 517045Sodium Acetate

Product 1

HCID 6765042-Methyl-1,3-benzoxazol-6-ol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1.5 grams (0.009 mole) of 4-((hydroxyimino)methyl)benzene-1,3-diol in 5 mL of DMF and 15 mL of acetonitrile was stirred and 1.3 mL (0.014 mole) of phosphorus oxychloride was added portionwise. Upon completion of addition the reaction mixture was stirred for an additional one hour. After this time the reaction mixture was stirred with ice and water that contained 3.0 grams of sodium acetate, and extracted with diethyl ether. The extract was washed with water, dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using mixtures of ethyl acetate and hexane, and finally 100% ethyl acetate, as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.75 gram of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure to a residue
  7. customThe residue was purified with column chromatography on silica gel using mixtures of ethyl acetate and hexane, and finally 100% ethyl acetate, as eluants
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ddca1599fdd94433a327372bf51ca4cb
Source dataset
uspto-grants-2007_04
Patent number
US07208450B2

Reaction notes

Loading…