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

HRID 924995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924995
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5](O)=[O:6].O.CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Komponenten

5

Edukt 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 143722353-Chloro-4-(methoxycarbonyl)benzoic acid

Produkt 1

HCID 19780655Methyl 2-chloro-4-(hydroxymethyl)benzoateAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
76 °C

Versuchsvorschrift

To a solution of 3-chloro-4-(methoxycarbonyl)benzoic acid (400 mg, 1.9 mmol) in anhydrous THF (15 mL) was added Borane methyl sulfide complex (10 M, 0.56 mL, 5.6 mmol). The resulting solution was heated at 76° C. for 6 hours. After being cooled, the mixture was slowly poured into water (40 mL) at −10° C., then followed a standard aqueous/EtOAc workup procedure to give crude product (350 mg, yield 94%).

Aufarbeitung

  1. temperatureAfter being cooled

Quellen und Nachweise

ORD-Eintrag
ord-ef3f67e6142f4a10b2952a8302f73001
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283229B2

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