Diethyl Ether → (1,1'-Biphenyl)-2,2'-dimethanol

HRID 132731Notes

Reaction equation

HRID 132731 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)C.[C:12]1([C:23]2[C:24]([C:29](OCC)=[O:30])=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:13]([C:18](OCC)=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=1>O>[C:23]1([C:12]2[C:13]([CH2:18][OH:19])=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:24]([CH2:29][OH:30])=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 13793399Diethyl diphenateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 243265(1,1'-Biphenyl)-2,2'-dimethanolYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3 g LiAlH4 was added 100 ml anhydrous ethyl ether. While cooling with ice-bath and stirring intensely, 0.05 mol diethyl 2,2′-biphenyldicarboxylate was slowly added dropwise. The reaction mixture was heated refluxing for 5 hours, then cooled. Excess LiAlH4 was decomposed with water. The mixture was filtered, and the filtrate was extracted with ethyl ether. The extract was dried over anhydrous sodium sulfate. The solvent was removed. Column chromatography gave 2,2′-biphenyldimethanol as a white solid, the yield was 75%, and m.p. was 98-103° C. IR spectrum had a strong absorption peak at 3400 cm−1, and had no absorption peak at about 1700 cm−1. This demonstrated that the reduction reaction was carried out completely.

Workup

  1. temperatureWhile cooling with ice-bath
  2. temperatureThe reaction mixture was heated
  3. temperaturerefluxing for 5 hours
  4. temperaturecooled
  5. filtrationThe mixture was filtered
  6. extractionthe filtrate was extracted with ethyl ether
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-ab470297c5914f69bc4375f8fe401930
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Reaction notes

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