Pyridine → HCID 13587813, compound

HRID 1789085Notes

Reaction equation

HRID 1789085 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:15]([O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30](Cl)=[O:31])=[CH:24][CH:23]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].N1C=CC=C[CH:34]=1>O>[CH3:34][CH:29]([CH2:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:23][CH:24]=1)[C:30]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)=[O:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 3454204-Fluoro-4'-hydroxybiphenylHCID 54506897HCID 54506897, compound

Product 1

HCID 13587813HCID 13587813, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Hydroxy-4'-fluorobiphenyl (2.1 g, 0.012 mol) was dissolved in pyridine (10 ml), and to the solution was added β-(4-hexyloxyphenyl)propionic acid chloride (3.0 g, 0.01 mol) with sufficient shaking, followed by allowing the resulting reaction solution to stand overnight, thereafter pouring it in water (100 ml), extracting the resulting oily material with toluene (100 ml), washing the toluene layer with 6N-HCl and then with 2N-NaOH, further washing with water till the washing liquid became neutral, filtering, distilling off toluene under reduced pressure, and recrystallizing residual crystals from ethanol to obtain the objective 4'-fluoro-4-biphenylyl α-methyl-β-(4-hexyloxyphenyl)propionate (2.1 g, yield 48%). m.p.: 78.4°-79.5° C. N-I point: 38.1° C.

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. washwith 2N-NaOH, further washing with water till the washing liquid
  5. filtrationfiltering
  6. distillationdistilling off toluene under reduced pressure
  7. customrecrystallizing residual crystals from ethanol

Sources & evidence

ORD record
ord-32ae5c7ca03e4dc381e964a85ea45d07
Source dataset
uspto-grants-1987_08
Patent number
US04686305

Reaction notes

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