Hydrochloric Acid → 3-(2-Hydroxyethyl)-2,3-dihydrobenzofuran-7-yloxyacetic acid

HRID 2186740Notes

Reaction equation

HRID 2186740 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]([O:17]C)=[O:16])[C:7]=2[O:6][CH2:5]1.[OH-].[Na+].Cl>CO>[OH:1][CH2:2][CH2:3][CH:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]([OH:17])=[O:16])[C:7]=2[O:6][CH2:5]1

Participants

5

Procedure

Methyl 3-(2-hydroxyethyl)-2,3-dihydrobenzofuran-7-yloxyacetate (7.80 g) was dissolved in methanol (100 ml), and a 2N sodium hydroxide aqueous solution (20 ml) was added to the resultant solution, and the mixture was stirred at room temperature for 4 hours. 1N hydrochloric acid (45 ml) was added to the reaction solution, and the mixture was concentrated. The residue was dissolved in ethyl acetate (200 ml), washed with water and saturated brine, and then dried over sodium sulfate. After sodium sulfate was filtered off, the filtrate was concentrated, and the residue was recrystallized from ethyl acetate/n-hexane to obtain the object compound (6.21 g, yield 84%).

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate (200 ml)
  3. washwashed with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter sodium sulfate was filtered off
  6. concentrationthe filtrate was concentrated
  7. customthe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-06ae478bdd104f46a32c5e3b2a78eddd
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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