Sodium Hydroxide → HCID 22238272, compound

HRID 1743194Notes

Reaction equation

HRID 1743194 reaction equation
C([O:4][C:5]1[C:6]([CH3:23])=[C:7]([CH3:22])[C:8]2[O:12][C:11]([CH3:13])=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:9]=2[C:20]=1[CH3:21])(=O)C.[OH-].[Na+]>O1CCCC1.CO>[CH3:13][C:11]1[O:12][C:8]2[C:7]([CH3:22])=[C:6]([CH3:23])[C:5]([OH:4])=[C:20]([CH3:21])[C:9]=2[C:10]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54005160HCID 54005160, compound

Product 1

HCID 22238272HCID 22238272, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2,4,6,7-tetramethyl-3-phenylbenzofuran-5-yl acetate (4.00 g, 13.0 mmol) in a mixture of tetrahydrofuran (32 mL) and methanol (8 mL) was added 8N sodium hydroxide solution (2.0 mL) dropwise and the mixture was stirred at 40° C. for 1 hour. The solvent was then distilled off under reduced pressure. To the residue was added 2N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from isopropyl ether-hexane to obtain the title compound (3.0 g, yield 87%).

Workup

  1. distillationThe solvent was then distilled off under reduced pressure
  2. additionTo the residue was added 2N hydrochloric acid
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from isopropyl ether-hexane

Sources & evidence

ORD record
ord-1a4293d1bffb4261a4f21b959ce82950
Source dataset
uspto-grants-2006_03
Patent number
US07008950B1

Reaction notes

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