4,5-Dimethylbenzene-1,2-diol → HCID 15125119, compound

HRID 373375Notes

Reaction equation

HRID 373375 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:10])[C:5](=[CH:7][C:8]=1[CH3:9])[OH:6].[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18](O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:14][CH:13]=1.[H-].C1(C)C=CC(S(O)(=O)=O)=CC=1.[Na+]>C1(C)C=CC=CC=1>[F:11][C:12]1[CH:13]=[CH:14][C:15]([CH:18]([C:3]2[C:2]([CH3:1])=[C:8]([CH3:9])[CH:7]=[C:5]([OH:6])[C:4]=2[OH:10])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 127302874,5-Dimethylbenzene-1,2-diolHCID 145139637-(4-Fluorophenyl)-7-hydroxyheptanoic acidHCID 23709171HCID 23709171, compound

Product 1

HCID 15125119HCID 15125119, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4,5-dimethylcatechol (663 mg) and 7-(4-fluorophenyl)-7-hydroxyheptanoic acid (1.15 g) in toluene (18 ml) was added sodium p-toluene sulfonate monohydride (455 ml) and the reaction was carried out at 100° C. for 20 hours. After cooling in air, the reaction mixture was extracted by addition of water and ethyl acetate. The organic layer was separated, washed in turn with water and saturated saline and dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by subjecting it to silica gel column chromatography and eluting with ethyl acetate/hexane (1:7) to obtain 7-(4-fluorophenyl)-7-(2,3-dihydroxy-5,6-dimethylphenyl)heptanoic acid (530 mg) (Compound 57). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Workup

  1. temperatureAfter cooling in air
  2. extractionthe reaction mixture was extracted by addition of water and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed in turn with water and saturated saline
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified
  8. washeluting with ethyl acetate/hexane (1:7)

Sources & evidence

ORD record
ord-f39ec43e07ff4e0d8d301cbe13afc7d3
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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