Sodium Hydroxide → HCID 59560462, compound

HRID 1643591Notes

Reaction equation

HRID 1643591 reaction equation
C[O:2][C:3]([C:5]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+]>CO>[F:23][C:21]1[CH:22]=[C:17]([CH:18]=[C:19]([F:24])[CH:20]=1)[O:16][C:14]1[C:8]2[CH2:9][C:10]([CH3:12])([CH3:13])[O:11][C:7]=2[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59560293HCID 59560293, compound

Product 1

HCID 59560462HCID 59560462, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(3,5-difluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (113a) (0.4 g, 0.0012 mol) in MeOH (5 mL) was added NaOH (0.5 g, 0.012 mol) in one portion. The mixture was stirred at room temperature overnight. TLC (EtOAc/petroleum ether=1/10) showed the starting material was still present. The mixture was refluxed for another 3 hrs. After TLC indicated the reaction was complete. The solvents were removed in vacuo. The residue was dissolved in water and acidified with conc. HCl to pH 1. The aqueous phase was extracted with EtOAc (2×15 mL). The organic phase was dried over Na2SO4 and concentrated to give an off-white solid (0.308 g, 80% yield).

Workup

  1. temperatureThe mixture was refluxed for another 3 hrs
  2. customThe solvents were removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionThe aqueous phase was extracted with EtOAc (2×15 mL)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8b4f8f14ee534ac4b4302c6cbc357be8
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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