反应 #68727

反应方程式

2

4-Bromomethyl benzophenone

calcium carbonate

→

3

收率 89.0%

4-Hydroxylmethyl benzophenone

收率 89.0%

溶剂

1,4 dioxane

water

反应条件

后处理

1. 1
   温度The mixture was heated
2. 2
   温度to reflux for 18 h
3. 3
   浓缩concentrated in vacuo
4. 4
   其他The organic layer was collected
5. 5
   干燥dried over MgSO4
6. 6
   浓缩concentrated in vacuo
7. 7
   其他then recrystalised from diethyl ether

实验过程

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%).

来源