Phenacyl bromide → 2-[2,5-Bis(benzyloxy)phenoxy]-1-phenylethanone

HRID 31214Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 31214
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[OH:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27].C(=O)([O-])O.[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[O:23][CH2:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6259Phenacyl bromideHCID 2855718-Crown-6HCID 516893Potassium BicarbonateHCID 155069722,5-Bis(benzyloxy)phenol

Produkt 1

HCID 179784822-[2,5-Bis(benzyloxy)phenoxy]-1-phenylethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

A mixture of 2,5-bis(benzyloxy)phenol (0.28 g), 2-bromoacetophenone (0.22 g), potassium hydrogen-carbonate (0.25 g) and 18-Crown-6 (3 mg) in acetonitrile (4.2 ml) was stirred at 22° C. for one week. The mixture was filtered and evaporated to dryness under reduced pressure. The residue was triturated with the mixture of ether (8.2 ml) and water (1.4 ml) at the ice bath temperature. The product was collected by filtration, washed with cold ether and dried under reduced pressure. Yield is 0.14 g. 1H NMR (DMSO-d6) δ=4.98 (s, 2H), 5.06 (s, 2H), 5.58 (s, 2H), 6.51 (dd, J=8.9, 2.3 Hz, 1H), 6.68 (d, J=2.3 Hz, 1H), 6.94 (d, J=8.9 Hz, 1H), 7.28-8.03 (m, 15H).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness under reduced pressure
  3. customThe residue was triturated with the mixture of ether (8.2 ml) and water (1.4 ml) at the ice bath temperature
  4. filtrationThe product was collected by filtration
  5. washwashed with cold ether
  6. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7f9a6aad03f3423b9c5a65a32fd0e897
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425568B2

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