Phenylacetic Acid → 4-(2-Mesyloxyethoxy)phenyl benzylketone

HRID 1738618

Reaktionsgleichung

Reaktionsgleichung von HRID 1738618
[CH3:1][S:2]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:4])=[O:3].[C:15]1([CH2:21]C(O)=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:25]1([CH:31]([CH2:35][CH3:36])[C:32](O)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[S:2]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:21]([C:32]([CH:31]([C:25]2[CH:30]=[CH:29][C:28]([O:8][CH2:7][CH2:6][O:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:27][CH:26]=2)[C:35]2[CH:36]=[CH:11][CH:10]=[CH:9][CH:14]=2)=[O:33])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)([CH3:1])(=[O:4])=[O:3]

Komponenten

4

Edukt 3

HCID 999Phenylacetic AcidHCID 70122-Phenylbutyric AcidHCID 2264992-Phenoxyethyl methanesulfonate

Produkt 1

HCID 867545724-(2-Mesyloxyethoxy)phenyl benzylketoneAusbeute 80 %

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

The oil comprising 2-Phenoxyethyl methanesulfonate was prepared as described above in Example 1. The acylation and workup procedure was identical to that of Example 1 with the exception that 30.26 g (220 mmol) 2-phenylacetic acid was reacted instead of the 2-phenylbutyric acid. The organic layer obtained by the workup procedure was cooled to 25° C. and stirred at this temperature for 1 hour. The resulting crystallized product was filtered, washed with toluene and dried under vacuum at 40° C. to yield 53.18 g (159 mmol) of the 4-(2-mesyloxyethoxy)phenyl benzylketone as a tan colored solid. Yield: 80% on 2-phenoxyethanol.

Aufarbeitung

  1. customwas prepared
  2. customThe organic layer obtained by the workup procedure
  3. customThe resulting crystallized product
  4. filtrationwas filtered
  5. washwashed with toluene
  6. customdried under vacuum at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-f59c121cca844a8bb94b070a82da3b2e
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05962743

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