O-Cresol → 2-(2-Methylphenoxy)benzoic acid

HRID 1198617Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1198617
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C1C=CC([I+][C:16]2[C:21]([C:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][CH:17]=2)=CC=1>CO.[OH-].[Na+]>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][C:21]=1[C:22]([OH:24])=[O:23]

Komponenten

5

Edukt 2

HCID 335O-CresolHCID 73883iodonium, (2-carboxyphenyl)phenyl-, inner salt

Produkt 1

HCID 2330382-(2-Methylphenoxy)benzoic acidAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of 2-methylphenol (III: R3 =H) (33 g, 305 mmol) in MeOH (100 mL) was treated with Na (2.1 g, 90 mmol), and excess MeOH was removed under reduced pressure. Diphenyliodonium-2-carboxylate (II: R1 =H) (19.6 g, 60 mmol) and cupric acetate (0.5 g) were added and the mixture was stirred at 90° C. for 10 h. The solution was diluted with 2N NaOH, filtered through celite and acidified with HCl. The mixture was then dissolved in 2N K2CO3 and extracted twice with EtOAc to remove excess 2-methylphenol. The aqueous layer was then poured into excess 2N HCl to give 2-(2-methylphenoxy)benzoic acid (IV: R1 =R3 =H) (8.85 g, 64%), suitable for the next step. A sample crystallized from ligroin, mp 133°-134° C. (Ber, 1905, 38, 2111 records mp 133.5° C.).

Aufarbeitung

  1. customwas removed under reduced pressure
  2. filtrationfiltered through celite
  3. dissolutionThe mixture was then dissolved in 2N K2CO3
  4. extractionextracted twice with EtOAc
  5. customto remove excess 2-methylphenol
  6. additionThe aqueous layer was then poured into excess 2N HCl

Quellen und Nachweise

ORD-Eintrag
ord-39e02fd31af6402a87b5b5a2da9f82e4
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05281620

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