Methanol → HCID 2750802, compound

HRID 1637565Notes

Reaction equation

HRID 1637565 reaction equation
[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])[C:3]([OH:5])=[O:4].[CH3:15]O>S(=O)(=O)(O)O>[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])[C:3]([O:5][CH3:15])=[O:4]

Participants

4

Reactant 2

HCID 887MethanolHCID 19044915HCID 19044915, compound

Product 1

HCID 2750802HCID 2750802, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Methyl 2-hydroxy-2-[2-nitrophenyl]acetate (FIG. 2; Compound 6) was prepared by dissolving crude acid 2-hydroxy-2-[2-nitrophenyl]acetic acid (entire amount) in methanol (100 ml). Sulfuric acid (5 drops) was added, and the mixture was refluxed for 2.5 hr. The solvent was then evaporated. The residue was taken up in ethyl acetate and extracted with saturated sodium bicarbonate, followed by water and brine. After drying over MgSO4, the solvent was evaporated to give 9.13 g (90%) of crude ester which was recrystallized from isopropyl ether to give 7.92 g (78%) of methyl 2-hydroxy-2-[2-nitrophenyl]acetate. mp. 69-71° C. 1H-NMR: 8.01 (d, J=8.19 Hz, 1H), 7.70-7.63 (m, 2H), 7.55-7.49 (m, 1H), 5.83 (d, J=4.88 Hz, 1H), 3.76 (s, 3H), 3.66 (d, J=4.89 Hz, 1H). HRMS(CI): calculated for C9H10NO5 [M+ +H] m/z=212.0559, observed 212.0555.

Workup

  1. temperaturethe mixture was refluxed for 2.5 hr
  2. customThe solvent was then evaporated
  3. extractionextracted with saturated sodium bicarbonate
  4. dry with materialAfter drying over MgSO4
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7cc7b6b6a3ce46f7bc8e3bae826651c3
Source dataset
uspto-grants-2000_03
Patent number
US06043065

Reaction notes

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