1-Chloro-4-(chloromethyl)benzene → HCID 86676534、化合物

HRID 73505ノート

反応式

HRID 73505 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.[OH:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[CH:14]=[O:15].C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=2[O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH:14]=[O:15])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 112306483-Hydroxy-4-[(4-methoxyphenyl)methoxy]benzaldehyde

生成物 1

HCID 86676534HCID 86676534、化合物収率 73.6%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 180Acetone溶媒

実験手順

A solution of 4-chlorobenzyl chloride (67.9 g), 3-hydroxy-4-(4-methoxy-benzyloxy)-benzaldehyde (40) (99 g) and tetrabutylammonium iodide (14.1 g) was heated at reflux in acetone (0.4 L) over solid potassium carbonate (39.1 g) for 3 hours. Excess acetone was removed by rotary evaporation under reduced pressure and the resulting residue partitioned between ethyl acetate and dilute hydrochloric acid (0.5 N). The organic layer was washed with water and brine and then dried over magnesium sulphate. Ethyl acetate was removed by rotary evaporation under reduced pressure to afford the crude product. The crude oil was triturated with a 50/50 mixture of diethyl ether and hexane accompanied by vigorous stirring to afford the product as a colourless solid (108 g, 73% yield, retention time 3.70 mins, poor ionization, ES− m/z 538.05). 1H NMR (400 MHz, CDCl3) δ 9.84 (s, 1H), 7.51-7.43 (m, 2H), 7.42-7.32 (m, 6H), 7.07 (d, J=8.1 Hz, 1H), 6.97-6.89 (m, 2H), 5.19 (s, 2H), 5.17 (s, 2H), 3.85 (s, 3H).

後処理

  1. customExcess acetone was removed by rotary evaporation under reduced pressure
  2. customthe resulting residue partitioned between ethyl acetate and dilute hydrochloric acid (0.5 N)
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customEthyl acetate was removed by rotary evaporation under reduced pressure
  6. customto afford the crude product
  7. customThe crude oil was triturated with a 50/50 mixture of diethyl ether and hexane

出典と根拠

ORDレコード
ord-ce12807a553c4e0aa6516372fa81cd19
出典データセット
uspto-grants-2014_09
特許番号
US08829184B2

反応ノート

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