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

HRID 1047875

반응식

HRID 1047875 반응식
[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

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 670444-Chlorophthalic anhydrideHCID 21226445Aluminium lithium hydride2회

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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)]

후처리

  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

출처 및 근거

ORD 기록
ord-8459d90f2a6f489588e4e05c599eaf25
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569535B2

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