Sodium Hydroxide → 3,3-Dimethyl-2,3-dihydrobenzofuran-6-carboxylic acid

HRID 445922Notes

Reaction equation

HRID 445922 reaction equation
[CH3:1][C:2]1([CH3:15])[C:6]2[CH:7]=[CH:8][C:9]([C:11]([O:13]C)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3]1.[OH-].[Na+]>CO>[CH3:1][C:2]1([CH3:15])[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58279528Methyl 3,3-dimethyl-2,3-dihydrobenzofuran-6-carboxylate

Product 1

HCID 582795703,3-Dimethyl-2,3-dihydrobenzofuran-6-carboxylic acidYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3,3-dimethyl-2,3-dihydrobenzofuran-6-carboxylate (0.116 g, 0.562 mmol) in MeOH (6 mL) at rt was added sodium hydroxide (1.969 mL, 1.969 mmol). The mixture was stirred at reflux for 1 h, and then concentrated under vacuum. The residue was diluted with water (20 mL) and extracted with ethyl acetate (2×40 mL). The combine extract was washed with brine (20 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product, 3,3-dimethyl-2,3-dihydrobenzofuran-6-carboxylic acid (0.105 g, 0.529 mmol, 94% yield), as a white solid.

Workup

  1. temperatureat reflux for 1 h
  2. concentrationconcentrated under vacuum
  3. additionThe residue was diluted with water (20 mL)
  4. extractionextracted with ethyl acetate (2×40 mL)
  5. extractionThe combine extract
  6. washwas washed with brine (20 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-d5149a2e163f4b7089f1ae1dc8188b24
Source dataset
uspto-grants-2013_07
Patent number
US08476430B2

Reaction notes

Loading…