Sodium Hydroxide → HCID 11075482, compound

HRID 413604Notes

Reaction equation

HRID 413604 reaction equation
[OH-].[Na+].[CH:3]([C:5]1[CH:20]=[CH:19][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])=[CH:7][C:6]=1[OH:21])=[O:4].C(Cl)(Cl)Cl.CO>CO>[CH:3]([C:5]1[CH:20]=[CH:19][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:7][C:6]=1[OH:21])=[O:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18533311HCID 18533311, compoundHCID 21584188Chloroform methanol

Product 1

HCID 11075482HCID 11075482, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2 N aqueous NaOH (10 mL) was added to ethyl 5-(4-formyl-3-hydroxyphenoxy)valerate (1.5 g, mw 266.3, 5.8 mmol; prepared as in Example 16) dissolved in methanol (20 mL) and 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 (50 mL), washed with ethyl acetate (3×15 mL, discarded), acidified to pH 4 with 6 N aqueous HCl, and extracted with ethyl acetate (4×25 mL). The combined organic extracts were washed with brine (2×50 mL), dried over Na2SO4, filtered, and concentrated to yield 1.35 g (98%) of a white solid. A portion of the solid was purified by flash chromatography on silica (CHCl3-methanol, 45:1) and recrystallized from boiling ethyl acetate-hexane to provide NMR and TLC (Rf origin) pure title product; 1H NMR (500 MHz, CDCl3, 294 K) δ11.47 (s), 9.71 (s), 7.42 (d, J=8.6; 1H), 6.53 (dd, J=2.3, 8.6; 1H), 6.41 (d, J=2.3; 1H), 4.04 (t, J=5.8; 2H), 2.46 (t, J=7.0; 2H), 1.86 (m; 4H).

Workup

  1. customMethanol was removed under reduced pressure
  2. additionthe reaction diluted with water (50 mL)
  3. washwashed with ethyl acetate (3×15 mL, discarded)
  4. extractionextracted with ethyl acetate (4×25 mL)
  5. washThe combined organic extracts were washed with brine (2×50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3db885782ac644949049f423ca730073
Source dataset
uspto-grants-2003_05
Patent number
US06566494B1

Reaction notes

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