Toluene → HCID 67826442, compound

HRID 846554Notes

Reaction equation

HRID 846554 reaction equation
[CH3:1][CH:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].O[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.C1(C)C=CC=CC=1.S(Cl)(Cl)=O>O>[C:12]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1.[CH3:1][CH:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 1140TolueneHCID 71034-HydroxybiphenylHCID 83142-Methylbutanoic AcidHCID 24386Thionyl Chloride2×

Product 1

HCID 67826442HCID 67826442, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.49 g of (+)-2-methylbutanoic acid,8.50 g of 4-hydroxy biphenyl and 20 ml of toluene were charged into a flask and then 4.0 ml (55 mmol) of thionyl chloride was added thereto with stirring. The resulting mixture was maintained at a temperature of 70°~80° C. and reacted for 8 hours. After the completion of the reaction, the resulting product was cooled to room temperature, added with water to decompose the excess amount of thionyl chloride, washed with water and dried on anhydrous magnesium sulfate. After the removal of solvent, it was purified by a column chromatography of silica gel to obtain 12.69 g of (+)-2-methylbutanoic acid biphenyl having an oily specific rotation [α]25 (16.46 wt% in chloroform) of +15.1°.

Workup

  1. temperatureThe resulting mixture was maintained at a temperature of 70°~80° C.
  2. customreacted for 8 hours
  3. customAfter the completion of the reaction
  4. washwashed with water
  5. dry with materialdried on anhydrous magnesium sulfate
  6. customAfter the removal of solvent, it
  7. customwas purified by a column chromatography of silica gel

Sources & evidence

ORD record
ord-50eb68cea4e14c11b4663cb90ac08145
Source dataset
uspto-grants-1992_08
Patent number
US05137653

Reaction notes

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