Water → Methyl 2-chloro-4-(hydroxymethyl)benzoate

HRID 1352097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1352097
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O-])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].O.C(OCC)(=O)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12]

Komponenten

5

Edukt 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 212765331,4-Benzenedicarboxylic acid, 2-chloro-, 1-methyl ester

Produkt 1

HCID 19780655Methyl 2-chloro-4-(hydroxymethyl)benzoateAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Borane-methyl sulfide complex (10 M; 10 Ml, 100 mmol) was added to a solution of 2-chloro-1,4-benzenedicarboxylic acid, 1-methyl ester (Example 1; 11.98 g, 55.8 mmol) in tetrahydrofuran (100Ml). The solution was heated at reflux for 2 h and then allowed to stand at room temperature overnight. It was poured into water and ethyl acetate (200 Ml each). The layers were separated and the aqueous layer was extracted with ethyl acetate (100 Ml). The combined organic layers were washed with brine (200 Ml), dried (MgSO4), filtered, and evaporated to give 2-chloro-4-(hydroxymethyl)benzoic acid, methyl ester (11.09 g, 99%) as a colorless oil.

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureat reflux for 2 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (100 Ml)
  5. washThe combined organic layers were washed with brine (200 Ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0ef0dc4f6a4f4db7970fcb1623f8efb7
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217728B2

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