Toluene → HCID 14669778, compound

HRID 1762771Notes

Reaction equation

HRID 1762771 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:25][CH:26]([CH2:37][CH3:38])[CH2:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1.C1(C)C=CC=CC=1>N1C=CC=CC=1>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([O:1][C:32](=[O:33])[C:31]3[CH:35]=[CH:36][C:28]([CH2:27][CH:26]([CH3:25])[CH2:37][CH3:38])=[CH:29][CH:30]=3)=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 2735083HCID 2735083, compoundHCID 10616140[1,1'-Biphenyl]-4-ol, 4'-(decyloxy)-

Product 1

HCID 14669778HCID 14669778, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

This 4-hydroxy-4'-n-decyloxybiphenyl (0.5 g) was dissolved in dry pyridine (20 ml), followed by dropwise adding to the solution, commercially available (+)-p-(2-methylbutyl)benzoyl chloride (0.4 g), further pouring dry toluene (15 ml) in the mixture, sufficiently shaking at room temperature, further heating on a water bath at 60° C. for 3 hours, cooling down to room temperature, adding toluene (50 ml), twice washing with 6N hydrochloric acid (100 ml), further twice washing with a 2N alkali aqueous solution, several times washing with saturated NaCl aqueous solution to make the liquid neutral, drying over sodium sulfate, distilling off toluene, filtering through active carbon on heating using a mixed solvent of ethanol (20 ml) and ethyl acetate (20 ml), recrystallizing, filtering crystals deposited in a refrigerator, and drying to obtain the objective 4-n-decyloxy-4'-(p-(2-methylbutyl)benzoyloxy)biphenyl (0.3 g). Its phase transition points are shown in Table 3, sample No. 10. Further, its values of elemental analysis accorded well with its theoretical values as follows:

Workup

  1. temperaturefurther heating on a water bath at 60° C. for 3 hours
  2. temperaturecooling down to room temperature
  3. washtwice washing with 6N hydrochloric acid (100 ml)
  4. washfurther twice washing with a 2N alkali aqueous solution, several times
  5. washwashing with saturated NaCl aqueous solution
  6. dry with materialdrying over sodium sulfate
  7. distillationdistilling off toluene
  8. filtrationfiltering through active carbon
  9. temperatureon heating
  10. customrecrystallizing
  11. filtrationfiltering crystals
  12. customdrying

Sources & evidence

ORD record
ord-8ccd7d4252a94d1e89e1cdace47f6129
Source dataset
uspto-grants-1989_05
Patent number
US04834907

Reaction notes

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