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

HRID 40449Notes

Reaction equation

HRID 40449 reaction equation
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

Participants

5

Reactant 2

HCID 10112Calcium CarbonateHCID 1229514-(Bromomethyl)benzophenone

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-3343e245b18d4cf9adf5e8d3d3017169
Source dataset
uspto-grants-2013_09
Patent number
US08530212B2

Reaction notes

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