Toluene → HCID 22157313, compound

HRID 1073472Notes

Reaction equation

HRID 1073472 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([OH:5])=[O:4].O[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.C1(C)C=CC=CC=1.S(Cl)(Cl)=O>O>[C:16]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1.[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 1140TolueneHCID 71034-HydroxybiphenylHCID 24386Thionyl Chloride2×HCID 942512-Methyloctanoic acid

Product 1

HCID 22157313HCID 22157313, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Then, 2.02 g (12.8 mmol) of the above (+)-2-methyl octanoic acid, 2.02 g (11.9 mmol) of 4-hydroxy biphenyl and 10 ml of toluene were charged into a flask, and further 1.0 ml (13.7 mmol) of thionyl chloride was added with stirring, which were then reacted for 9 hours while maintaining at a temperature of 70°~80° C. After the completion of the reaction, the reaction mixture was cooled to room temperature, added with water to decompose excess thionyl chloride, washed with water and then dried on anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified through a column chromatography of silica gel to obtain 3.43 g of an oily (+)-biphenyl-2-methyloctanoate having a specific rotary power [α]25D =+16.3° (2.6% by weight, in chloroform).

Workup

  1. customwhich were then reacted for 9 hours
  2. temperaturewhile maintaining at a temperature of 70°~80° C
  3. customAfter the completion of the reaction
  4. washwashed with water
  5. dry with materialdried on anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled off
  7. customthe residue was purified through a column chromatography of silica gel

Sources & evidence

ORD record
ord-f4eeb005f17e46479cdc908139d87445
Source dataset
uspto-grants-1990_11
Patent number
US04970023

Reaction notes

Loading…