Sodium Hydroxide → HCID 57483850, compound

HRID 384402Notes

Reaction equation

HRID 384402 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[C:11]=2[O:19][CH3:20])[O:7][C:6]=1[CH3:21])=[O:4].[OH-].[Na+]>CO>[CH3:20][O:19][C:11]1[C:12]([N+:16]([O-:18])=[O:17])=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]1[O:7][C:6]([CH3:21])=[C:5]([C:3]([OH:4])=[O:2])[CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57483849HCID 57483849, compound

Product 1

HCID 57483850HCID 57483850, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

5-(2-Methoxy-3-nitro-phenyl)-2-methyl-furan-3-carboxylic acid methyl ester 53b (650 mg, 2.23 mmol) was dissolved in methanol, followed by addition of sodium hydroxide (268 mg, 6.7 mmol). Upon completion of the addition, the reaction mixture was stirred at 50° C. for 3 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure and adjusted to pH 3˜4 with 1 N hydrochloric acid to form a copious amount of precipitates. The mixture was filtered and the filter cake was recrystallized from a solvent mixture of hexane/ethyl acetate (V:V=5:1) to obtain the title compound 5-(2-methoxy-3-nitro-phenyl)-2-methyl-furan-3-carboxylic acid 53c (450 mg, yield 84%) as a white solid.

Workup

  1. additionUpon completion of the addition
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto form a copious amount
  4. customof precipitates
  5. filtrationThe mixture was filtered
  6. customthe filter cake was recrystallized from a solvent mixture of hexane/ethyl acetate (V:V=5:1)

Sources & evidence

ORD record
ord-5ca404c400f8404dbd18dd25b98df6dd
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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