Sodium Sulfate → 3-Hydroxymethyl-4,4'-dimethylbiphenyl

HRID 22249Notes

Reaction equation

HRID 22249 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=[CH:10][C:9]=1[C:21](OCC)=[O:22].S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[OH:22][CH2:21][C:9]1[CH:10]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:12]=[CH:13][C:8]=1[CH3:7]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 19430269Ethyl 4,4'-dimethylbiphenyl-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 183888713-Hydroxymethyl-4,4'-dimethylbiphenyl

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (0.2 g) in 50 ml of ether at 0° C. was added dropwise a solution of ethyl 4,4'-dimethylbiphenyl-3-carboxylate (2 g) in ether. After the addition was complete, the mixture was allowed to slowly rise to room temperature, and stirred for 2 hours. Excess reagent was hydrolysed with wet sodium sulfate. The mixture was filtered, the solvent evaporated from the filtrate under reduced pressure, and the residue flash-chromatographed on silica gel, eluting with 25% ethyl acetate in heptane, to yield 3-hydroxymethyl-4,4'-dimethylbiphenyl as an oil.

Workup

  1. additionAfter the addition
  2. customto slowly rise to room temperature
  3. filtrationThe mixture was filtered
  4. customthe solvent evaporated from the filtrate under reduced pressure
  5. customthe residue flash-chromatographed on silica gel
  6. washeluting with 25% ethyl acetate in heptane

Sources & evidence

ORD record
ord-1ddaf75f0e214d078ad914f5880ab475
Source dataset
uspto-grants-1995_06
Patent number
US05428037

Reaction notes

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