Pyridine → HCID 13627682, compound

HRID 1789086Notes

Reaction equation

HRID 1789086 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:17]([O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31](Cl)=[O:32])=[CH:25][CH:24]=1)[CH2:18][CH2:19][CH2:20][CH3:21].N1C=CC=C[CH:35]=1>O>[CH3:35][CH:30]([CH2:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:24][CH:25]=1)[C:31]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)=[O:32]

Participants

5

Reactant 3

HCID 1049PyridineHCID 136276804'-Propyl[1,1'-biphenyl]-4-olHCID 53826862HCID 53826862, compound

Product 1

HCID 13627682HCID 13627682, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Hydroxy-4'-propylbiphenyl (2.5 g, 0.012 mol) was dissolved in pyridine (10 ml) and to the solution was added β-(4-pentyloxyphenyl)propionic acid chloride (2.5 g, 0.01 mol) with sufficient shaking, followed by allowing the resulting reaction solution to stand overnight, pouring it in water (100 ml), extracting the resulting oily material with toluene (100 ml), washing the toluene layer with 6N-HCl, then with 2N-NaOH and further with water till the washing water became neutral, filtering, distilling off toluene under reduced pressure, and recrystallizing residual crystals from ethanol to obtain the objective 4'-propyl-4-biphenylyl α-methyl-β-(4-pentyloxyphenyl)propionate. m.p. 84.0°-84.5° C. N-I point 46.0° C. (extrapolated value).

Workup

  1. customthe resulting reaction solution
  2. extractionextracting the resulting oily material with toluene (100 ml)
  3. washwashing the toluene layer with 6N-HCl
  4. filtrationfiltering
  5. distillationdistilling off toluene under reduced pressure
  6. customrecrystallizing residual crystals from ethanol

Sources & evidence

ORD record
ord-149cf621368447ca9478e75c0d11594b
Source dataset
uspto-grants-1987_08
Patent number
US04686305

Reaction notes

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