4,5-Dichlorophthalic acid → (4,5-Dichloro-1,2-phenylene)dimethanol

HRID 1018824

反応式

HRID 1018824 の反応式
O1CCCC1.B.[Cl:7][C:8]1[CH:9]=[C:10]([C:18](O)=[O:19])[C:11](=[CH:15][C:16]=1[Cl:17])[C:12](O)=[O:13]>O1CCCC1>[Cl:7][C:8]1[C:16]([Cl:17])=[CH:15][C:11]([CH2:12][OH:13])=[C:10]([CH2:18][OH:19])[CH:9]=1

参加物

4

反応物 2

HCID 926004,5-Dichlorophthalic acidHCID 2723981Borane;tetrahydrofuran

生成物 1

HCID 13096434(4,5-Dichloro-1,2-phenylene)dimethanol収率 100.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of borane tetrahydrofuran complex (45 mL of 1.5 M solution in tetrahydrofuran/diethyl ether) cooled to 0° C. under nitrogen was added a solution of 4,5-dichlorophthalic acid (5.013 g; 21.1 mmol) in tetrahydrofuran (35 mL) dropwise over a 20 minute period. At the end of the addition, the mixture was allowed to stir for 2.5 h at 0° C. The mixture was quenched by slow addition of methanol until gas evolution ceased. The mixture was allowed to stir at room temperature for 30 minutes and the solvent removed in vacuo. The residue was taken up into ethyl acetate, washed with saturated sodium bicarbonate solution followed by brine solution. The organic extract was dried (sodium sulfate), filtered and concentrated in vacuo to give 4.41 g (100%) of 4,5-dichloro-1,2-di-hydroxymethyl benzene as a white solid: ES-LRMS calcd for C8H7C12O2 (M+−1) 205, found 205.

後処理

  1. additionAt the end of the addition
  2. customThe mixture was quenched by slow addition of methanol until gas evolution
  3. stirringto stir at room temperature for 30 minutes
  4. customthe solvent removed in vacuo
  5. washwashed with saturated sodium bicarbonate solution
  6. extractionThe organic extract
  7. dry with materialwas dried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5def08634dfe4c3382c14b4c98f5da67
出典データセット
uspto-grants-2002_11
特許番号
US06482951B2

関連ノート

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