Benzyl Salicylate → Benzyl 2-[2,6-Bis(isopropyl)phenoxycarbonyloxy]-benzoate

HRID 1766140

Reaktionsgleichung

Reaktionsgleichung von HRID 1766140
[C:1]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(N(CC)CC)C.[CH:25]([C:28]1[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]([CH3:40])[CH3:39])[C:29]=1[O:30][C:31](Cl)=[O:32])([CH3:27])[CH3:26]>ClCCl.CN(C1C=CN=CC=1)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH:25]([C:28]1[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]([CH3:40])[CH3:39])[C:29]=1[O:30][C:31]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:32])([CH3:27])[CH3:26]

Komponenten

7

Edukt 3

HCID 8363Benzyl SalicylateHCID 8471TriethylamineHCID 2716192,6-Di(propan-2-yl)phenyl carbonochloridate

Produkt 1

HCID 21110017Benzyl 2-[2,6-Bis(isopropyl)phenoxycarbonyloxy]-benzoateAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 311Citric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a cooled (0° C.) solution of benzyl salicylate (0.77 g, 3.3 mmol) in dichloromethane (6 mL) was added triethylamine (0.52 mL, 3.7 mmol) and a catalytic amount of DMAP. To this mixture a suspension of compound (104) (0.9 g, 3.7 mmol, crude product from last step) in dichloromethane (4 mL) was further added. The reaction was allowed to warm to room temperature slowly and stirred for 14 h. The reaction mixture was then diluted with 10% aqueous citric acid solution (10 mL) and extracted with ethyl ether (2×40 mL). The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was purified by radial chromatography on silica gel (eluting with ethyl acetate/hexane) to afford 0.8 g (57% yield over two steps) of the title compound (105).

Aufarbeitung

  1. additionwas further added
  2. extractionextracted with ethyl ether (2×40 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by radial chromatography on silica gel (eluting with ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-aa5bbd4bab1142a59edfe362c9369a13
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230003B2

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