Sodium Hydroxide → 3-(Ethoxycarbonyl)-5-(hydroxymethyl)benzoic acid

HRID 732517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732517
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:15]=[C:14]([CH2:16][OH:17])[CH:13]=[C:7]([C:8]([O:10]CC)=[O:9])[CH:6]=1)[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:15]=[C:14]([CH2:16][OH:17])[CH:13]=[C:7]([C:8]([OH:10])=[O:9])[CH:6]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 610139Diethyl 5-(hydroxymethyl)isophthalate

Produkt 1

HCID 210858293-(Ethoxycarbonyl)-5-(hydroxymethyl)benzoic acidAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Add commercially available 5-hydroxymethyl-isophthalic acid diethyl ester (5 g, 19.8 mmol) and NaOH (0.79 g, 19.8 mmol) to ethanol (100 mL). Stir for 4 h at room temperature. Concentrate and pour the residue into water (100 mL) and diethyl ether (100 mL). Separate the aqueous layer and wash it with diethyl ether (40 mL). Acidify the aqueous layer with 5 N HCl to about pH=1. Extract the acidic solution with ethyl acetate (3×40 mL). Wash the combined organic layers with water, saturated aqueous sodium chloride, dry (sodium sulfate) and concentrate to give the title compound as a solid (3.3 g, 74%).

Aufarbeitung

  1. concentrationConcentrate
  2. additionpour the residue into water (100 mL) and diethyl ether (100 mL)
  3. customSeparate the aqueous layer
  4. washwash it with diethyl ether (40 mL)
  5. extractionExtract the acidic solution with ethyl acetate (3×40 mL)
  6. washWash the combined organic layers with water, saturated aqueous sodium chloride
  7. dry with materialdry (sodium sulfate)
  8. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-24aa5fc3c4074e94ac0512758b249ce9
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585885B2

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