Pyridine → HCID 23125865, compound

HRID 132732

Reaction equation

HRID 132732 reaction equation
[C:1]1([C:9]2[C:10]([CH2:15][OH:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:2]([CH2:7][OH:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.N1C=C[CH:20]=[CH:19][CH:18]=1.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[O:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>>[C:23]([O:16][CH2:15][C:10]1[C:9]([C:1]2[C:2]([CH2:7][O:8][C:36](=[O:32])[C:35]3[CH:20]=[CH:19][CH:18]=[CH:33][CH:34]=3)=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 243265(1,1'-Biphenyl)-2,2'-dimethanol

Product 1

HCID 23125865HCID 23125865, compoundYield 93%

Procedure

To 0.03 mol 2,2′-biphenyldimethanol was added 30 ml tetrahydrofuran and 0.09 mol pyridine, then added 0.075 mol benzoyl chloride with stirring. The reaction mixture was heated refluxing for 4 hours, cooled and added 20 ml saturated saline. The mixture was extracted with ethyl acetate, and extract was dried over anhydrous sodium sulfate. The solvent was removed. Column chromatography gave 2,2′-biphenyldimethanol dibenzoate as a colorless viscous liquid, and the yield was 93%.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturerefluxing for 4 hours
  3. temperaturecooled
  4. additionadded 20 ml saturated saline
  5. extractionThe mixture was extracted with ethyl acetate
  6. extractionextract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-95eff78e70df4997a65f9cd5b2102bbd
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Linked notes

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