Methanol → HCID 18945367, compound

HRID 399850Notes

Reaction equation

HRID 399850 reaction equation
CC1(C)[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N+:19]([O-:21])=[O:20])[CH:8]=2)=N1.C[OH:24].O>S(=O)(=O)(O)O>[N+:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:4]([O:5][CH3:6])=[O:24])([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 962WaterHCID 18945219HCID 18945219, compound

Product 1

HCID 18945367HCID 18945367, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

4,4-Dimethyl-2-[3-(2-nitrophenyl)phenyl]4,5-dihydrooxazole (1.7 g) was heated to reflux for 19 hours in 95% methanolic sulfuric acid (28.7 ml) (prepared by mixing methanol (15 ml), concentrated sulfuric acid (1.15 ml), and water (1.44 ml) and bringing the total volume to 28.7 ml with additional methanol). After cooling, the solution was concentrated to ca. 7 ml and poured into ether (60 ml). The ethereal solution was washed with aqueous potassium carbonate solution and brine,then dried over magnesium sulfate and concentrated in vacuo to yield methyl 3-(2-nitrophenyl)benzoate as a yellow solid.

Workup

  1. customprepared
  2. temperatureAfter cooling
  3. concentrationthe solution was concentrated to ca. 7 ml
  4. additionpoured into ether (60 ml)
  5. washThe ethereal solution was washed with aqueous potassium carbonate solution and brine,then
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-41d6a1d6a01642fea2960147afd3e1a7
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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