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

HRID 1018824

반응식

HRID 1018824 반응식
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

참가 물질

4

반응물 2

HCID 926004,5-Dichlorophthalic acidHCID 2723981Borane;tetrahydrofuran

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5def08634dfe4c3382c14b4c98f5da67
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06482951B2

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