Isopropanol → 4-Acetoxy-2-isopropoxy-benzoic acid methyl ester

HRID 603980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 603980
[CH:1](O)([CH3:3])[CH3:2].[CH3:5][O:6][C:7](=[O:19])[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15](=[O:17])[CH3:16])=[CH:10][C:9]=1[OH:18].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>ClCCl>[CH3:5][O:6][C:7](=[O:19])[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15](=[O:17])[CH3:16])=[CH:10][C:9]=1[O:18][CH:1]([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 579902174-Acetoxy-2-hydroxy-benzoic acid methyl ester

Produkt 1

HCID 670554964-Acetoxy-2-isopropoxy-benzoic acid methyl esterAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Isopropanol (0.63 mL, 8.2 mmol) was added to a mixture of 4-Acetoxy-2-methoxy-benzoic acid methyl ester (Step 1, Example 299, 1.18 g, 5.6 mmol), Ph3P (1.84 g, 7.0 mmol), and dichloromethane (15 mL). Then DEAD (1.12 mL, 7.1 mmol) was added to the reaction. Reaction was stirred at room temperature for two days. Reaction solution was concentrated by rotary evaporation and the resulting residue was purified with silica gel prep plates and 1:5 EtOAc/Hexane as eluent. Obtained 1.11 g of 4-Acetoxy-2-isopropoxy-benzoic acid methyl ester in 79% yield.

Aufarbeitung

  1. customReaction
  2. customReaction solution
  3. concentrationwas concentrated by rotary evaporation
  4. customthe resulting residue was purified with silica gel prep plates and 1:5 EtOAc/Hexane as eluent

Quellen und Nachweise

ORD-Eintrag
ord-518b326e896c402eb13cc737ba4d4ad2
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906548B2

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