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

HRID 863900

반응식

HRID 863900 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:12](O)=[O:13])[C:5](=[CH:9][C:10]=1[Cl:11])[C:6](O)=[O:7].B.CSC>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[C:5]([CH2:6][OH:7])=[CH:9][C:10]=1[Cl:11]

참가 물질

3

반응물 2

HCID 926004,5-Dichlorophthalic acidHCID 12423031(Dimethyl sulfide)trihydroboron

생성물 1

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

반응 조건

온도
0 °C

실험 절차

A 1.24 g portion of 4,5-dichlorophthalic acid is dissolved in 40 mL anhydrous tetahydrofuran and the solution is cooled to 0° C. To this solution is slowly added 4 mL of borane-methyl sulfide. The reaction flask is first warmed to room temperature, then heated to reflux for 12 hours. The product mixture is cooled to 0° C., then slowly quenched with 50 mL methyl alcohol. Following removal of the solvent, the residue is partitioned between 40 mL water, and 100 mL 1:1 ethyl acetate tetrahydrofuran. The organic layer is washed with 30 mL brine, then dried over magnesium sulfate. Purification by silica gel chromatography (2:1 ethyl acetate/hexane) affords 1.01 g of the desired product as a white solid, m.p. 128°-136° C. MS(Hi res): m/z Calcd for C8H8Cl2O2 205.9901 Found 205.9872

후처리

  1. temperatureThe reaction flask is first warmed to room temperature
  2. temperatureheated
  3. temperatureto reflux for 12 hours
  4. temperatureThe product mixture is cooled to 0° C.
  5. customslowly quenched with 50 mL methyl alcohol
  6. customremoval of the solvent
  7. customthe residue is partitioned between 40 mL water, and 100 mL 1:1 ethyl acetate tetrahydrofuran
  8. washThe organic layer is washed with 30 mL brine
  9. dry with materialdried over magnesium sulfate
  10. customPurification by silica gel chromatography (2:1 ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-19d0d4ea4a1f48f8a1d8a0c6bbe7ef17
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05561141

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