Sodium Hydroxide → HCID 22313323, compound

HRID 965846Notes

Reaction equation

HRID 965846 reaction equation
[CH3:1][CH:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([O:14]C)=[O:13])[CH:8]=2)[O:3]1.[OH-].[Na+]>CO>[CH3:1][CH:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([OH:14])=[O:13])[CH:8]=2)[O:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22313331HCID 22313331, compound

Product 1

HCID 22313323HCID 22313323, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of methyl 2-methyl-2H-chromene-6-carboxylate (225 mg, 1.10 mmol) in MeOH (5 mL) is added NaOH (5 mL of a 5% aqueous solution). The mixture is heated in a 60° C. oil bath for 40 min, followed by cooling to rt. The methanol is removed in vacuo and the remaining aqueous layer is acidified to pH=5 with 1N HCl. The solution is extracted with EtOAc (2×), washed with brine, dried (MgSO4) and concentrated in vacuo to afford 209 mg (100%) of 2-methyl-2H-chromene-6-carboxylic acid as a yellow oil: 1H NMR (400 MHz, DMSO-d6) δ 13-12, 7.68, 7.65, 6.80, 6.53, 5.85, 5.10, 1.37.

Workup

  1. temperatureby cooling to rt
  2. customThe methanol is removed in vacuo
  3. extractionThe solution is extracted with EtOAc (2×)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f443d45323c24036a73af0322f2b697a
Source dataset
uspto-grants-2005_10
Patent number
US06951868B2

Reaction notes

Loading…