Sodium Hydroxide → HCID 22935584, compound

HRID 1272276Notes

Reaction equation

HRID 1272276 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:5]=1[O:6][C:7]([CH3:13])([CH3:12])[C:8]([O:10]C)=[O:9]>CO>[CH3:3][C:4]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:5]=1[O:6][C:7]([CH3:13])([CH3:12])[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22935573HCID 22935573, compound

Product 1

HCID 22935584HCID 22935584, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution of 8N sodium hydroxide (30 mL, 240 mmol) was added to a solution of methyl 2-(2,3,5-trimethylphenoxy)isobutyrate (29.0 g, 123 mmol) obtained in Reference Example 9 in methanol (290 ml) at room temperature and the mixture was stirred for 12 hours. The resulting mixture was concentrated under reduced pressure, and the residue was diluted with water. The aqueous layer was acidified by hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with water and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was crystallized from hexane to obtain 20.5 g (yield 75%) of the title compound. mp. 91–94° C.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-c4cb921f6f3745449518159035b6c74d
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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