Water → (4-Chloro-1,2-phenylene)dimethanol

HRID 1047875

反応式

HRID 1047875 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=O)[O:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][OH:7])=[C:4]([CH2:9][OH:8])[CH:3]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 670444-Chlorophthalic anhydrideHCID 21226445Aluminium lithium hydride2 回

生成物 1

HCID 10899147(4-Chloro-1,2-phenylene)dimethanol収率 94.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of 4-chlorophthalic anhydride (24.83 g, 136.01 mmol) in tetrahydrofuran (100 mL) is added dropwise to a mechanically stirred suspension of LAH (8.72 g, 229.78 mmol) in tetrahydrofuran (500 mL). After stirring overnight at room temperature, the excess LAH is decomposed by cautious addition of water (8.5 mL), 10% aqueous NaOH (17 mL) and water (8.5 mL). The reaction is diluted with tetrahydrofuran (300 mL) and the solids are removed by filtration through a celite pad and washed with tetrahydrofuran. The combined filtrate and wash is concentrated in vacuo on a rotary evaporator to afford diol 257 as a colorless liquid (22.16 g) that crystallized on standing. Crystallization is effected in benzene. [O. Farooq, Synthesis, 1035-1036 (1994); R. F. Bird, E. E. Turner, J. Chem. Soc. 5050-5051 (1952); J. Tirouflet, Compt. rend., 238, 2246-2247 (1954)]

後処理

  1. customthe solids are removed by filtration through a celite pad
  2. washwashed with tetrahydrofuran
  3. washThe combined filtrate and wash
  4. concentrationis concentrated in vacuo on a rotary evaporator

出典と根拠

ORDレコード
ord-8459d90f2a6f489588e4e05c599eaf25
出典データセット
uspto-grants-2013_10
特許番号
US08569535B2

関連ノート

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