Sodium Hydroxide → HCID 59726101, compound

HRID 336430Notes

Reaction equation

HRID 336430 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:5]([C:6]([O:8]C)=[O:7])=[C:4]([N+:13]([O-:15])=[O:14])[C:3]=1[O:16][CH3:17].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:13]([O-:15])=[O:14])[C:3]=1[O:16][CH3:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59726037HCID 59726037, compound

Product 1

HCID 59726101HCID 59726101, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the methyl ester 2-2 (9.90 g, 35.3 mmol) in MeOH (150 mL) was added 2N NaOH (150 mL) and the reaction was heated to reflux for 2.5 h. Methanol was removed in vacuo and the mixture was extracted with EtOAc. The aqueous layer was acidified to pH 2 with a concentrated solution of HCl and then extracted into EtOAc (×3). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to provide the acid 2-1 as an orange solid (8.84 g, 94% yield). 1H NMR (400 MHz, d6-DMSO) δ 3.83 (s, 3H), 3.95 (s, 3H), 8.23 (s, 1H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2.5 h
  3. customMethanol was removed in vacuo
  4. extractionthe mixture was extracted with EtOAc
  5. extractionextracted into EtOAc (×3)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c32d9b29eaef4ce4acc1c8b7f92d6497
Source dataset
uspto-grants-2014_11
Patent number
US08889695B2

Reaction notes

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