Sodium Hydroxide → HCID 18533309, compound

HRID 413606Notes

Reaction equation

HRID 413606 reaction equation
[OH-].[Na+].[CH:3]([C:5]1[CH:20]=[C:19]([CH3:21])[C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])=[C:7]([CH3:22])[CH:6]=1)=[O:4].C(Cl)(Cl)Cl.CO>CO>[CH:3]([C:5]1[CH:20]=[C:19]([CH3:21])[C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[C:7]([CH3:22])[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18533316HCID 18533316, compoundHCID 21584188Chloroform methanol

Product 1

HCID 18533309HCID 18533309, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2 N aqueous NaOH (30 mL) was added to ethyl 5-(4-formyl-2,6-dimethylphenoxy)valerate (4.0 g, mw 278.4, 14 mmol; prepared as in Example 18) dissolved in methanol (40 mL) and that the solution stirred at 25° C. for 1 hour, at which point TLC (CHCl3-methanol, 99:1) indicated the reaction was complete. Methanol was removed under reduced pressure and the reaction diluted with water (150 mL), washed with ethyl acetate (2×25 mL, discarded), acidified to pH 4 with 6 N aqueous HCl, and extracted with ethyl acetate (3×30 mL). The organic extract was washed with brine (2×75 mL), dried over Na2SO4, filtered and concentrated to yield 3.57 g (99%) of an amber oil. A portion of the oil was purified by flash chromatography on silica (CHCl3-methanol, 45:1) to provide NMR and TLC (Rf origin) pure title product:

Workup

  1. customMethanol was removed under reduced pressure
  2. additionthe reaction diluted with water (150 mL)
  3. washwashed with ethyl acetate (2×25 mL, discarded)
  4. extractionextracted with ethyl acetate (3×30 mL)
  5. extractionThe organic extract
  6. washwas washed with brine (2×75 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d75690f0ab504c8da08015f1b0e1226c
Source dataset
uspto-grants-2003_05
Patent number
US06566494B1

Reaction notes

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