Sodium Hydroxide → 7-Benzyloxy-2-ethylchromane-2-carboxylic acid

HRID 51088Notes

Reaction equation

HRID 51088 reaction equation
C(O[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH2:24][CH3:25])([C:19]([O:21]CC)=[O:20])[CH2:13][CH2:12]2)C1C=CC=CC=1.[OH-:26].[Na+]>C(O)(C)C>[CH2:12]([O:26][C:18]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][C:14]([CH2:24][CH3:25])([C:19]([OH:21])=[O:20])[O:15]2)=[CH:10][CH:9]=1)[C:11]1[CH:16]=[CH:17][CH:18]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22737373Ethyl 6-benzyloxy-2-ethylchromane-2-carboxylate

Product 1

HCID 112783807-Benzyloxy-2-ethylchromane-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

To a 2 L isopropanol solution of ethyl 6-benzyloxy-2-ethylchromane-2-carboxylate (155 g, 0.455 mol) was added 1 L of aqueous 5N sodium hydroxide. This solution was heated to 70° C. overnight. Isopropanol was removed under reduced pressure. The residue was acidified with conc. hydrochloric acid 300 ml and 2N hydrochloric acid to pH 1. The acidic solution was extracted three times with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated to give a yellow oil, which crystallized upon standing: 130 g (91%).

Workup

  1. customIsopropanol was removed under reduced pressure
  2. extractionThe acidic solution was extracted three times with AcOEt
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow oil, which
  7. customcrystallized

Sources & evidence

ORD record
ord-53fdc51ee23240fc85bd5c97d35e2d0b
Source dataset
uspto-grants-2004_03
Patent number
US06713508B2

Reaction notes

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