Calcium Carbonate → (4-(Hydroxymethyl)phenyl)(phenyl)methanone

HRID 40449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 40449
Br[CH2:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.C(=O)([O-])[O-:18].[Ca+2]>O1CCOCC1.O>[OH:18][CH2:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1

Komponenten

5

Edukt 2

HCID 10112Calcium CarbonateHCID 1229514-(Bromomethyl)benzophenone

Produkt 1

HCID 13149642(4-(Hydroxymethyl)phenyl)(phenyl)methanoneAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a suspension of 2 (6.0 g, 22 mmol) in a mixture of 1,4 dioxane (60 ml) and water (60 ml) was added calcium carbonate (10.8 g, 110 mmol). The mixture was heated to reflux for 18 h, concentrated in vacuo and the residue portioned between DCM and water. The organic layer was collected, dried over MgSO4, concentrated in vacuo then recrystalised from diethyl ether to furnish 3 (4.1 g, 89%) as a white solid; M.P. 59-61° C. (Lit 61-64° C.); δH (CDCl3) 3.14 (s, 1H, CH2OH), 4.75 (s, 2H, CH2OH), 7.41-7.49 (m, 4H, 3-, 3′-, 5-, 5′-H), 7.54-7.58 (m, 1H, 4′-H), 7.72-7.76 (m, 4H, 2-, 2′-, 6-, 6′-H) ppm; δC (CDCl3) 64.4 (CH2OH), 126.4 (3′-, 5′-C), 128.3 (3-, 5-C), 130.0, 130.4 (2-, 2′-, 6-, 6′-C), 132.5 (4′-C), 136.4, 137.5 (1-, 1′-C), 140.0 (4-C), 196.9 (Ar2C═O) ppm; νmax (thin film) 3406, 3058, 2921, 1655, 1279 cm−1; m/z (ES) 211 ([M−H]− 100%), 183 (45%).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 h
  3. concentrationconcentrated in vacuo
  4. customThe organic layer was collected
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customthen recrystalised from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3343e245b18d4cf9adf5e8d3d3017169
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530212B2

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