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

HRID 863900

Reaction equation

HRID 863900 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
0 °C

Procedure

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

Workup

  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)

Sources & evidence

ORD record
ord-19d0d4ea4a1f48f8a1d8a0c6bbe7ef17
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Linked notes

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