Sodium Hydroxide → HCID 86744478, compound

HRID 703512Notes

Reaction equation

HRID 703512 reaction equation
[OH-].[Na+].[CH3:3][C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:17]=[CH:16][O:15][C:14]=2[C:18]([O-:20])=[O:19])=[CH:9][CH:8]=1)([CH3:6])[CH3:5]>O.O1CCCC1>[CH3:6][C:4]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:17]=[CH:16][O:15][C:14]=2[C:18]([OH:20])=[O:19])=[CH:11][CH:12]=1)([CH3:3])[CH3:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86744479HCID 86744479, compound

Product 1

HCID 86744478HCID 86744478, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (1.42 g) in water (17.75 ml) was added to a vigorously stirred solution of methyl 5-(4-(1,1-dimethylethyl)phenylfuran-2-carboxylate (4.579 g) in tetrahydrofuran (100 ml) and stirred at room temperature for 17 hours, the solvent was removed in vacuo and the residue dissolved in 10% sodium hydrogen carbonate solution (200 ml) then acidified with 2 M hydrochloric acid. The mixture was extracted with diethyl ether (3 x 200 ml), the ether washed with water and dried (MgSO4) The solvent was removed in vacuo to give 5-(4-(1,1-dimethylethyl)phenylfuran-2-carboxylic acid, m.p. 230° C.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in 10% sodium hydrogen carbonate solution (200 ml)
  3. extractionThe mixture was extracted with diethyl ether (3 x 200 ml)
  4. washthe ether washed with water
  5. dry with materialdried (MgSO4) The solvent
  6. customwas removed in vacuo

Sources & evidence

ORD record
ord-969f87f2b89445c9a449af018d02109e
Source dataset
uspto-grants-1991_01
Patent number
US04983619

Reaction notes

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