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

HRID 1078775

反応式

HRID 1078775 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-44c620507ef6414485abd25e1d4515ba
出典データセット
uspto-grants-1996_08
特許番号
US05550149

関連ノート

読み込み中…