4-Cyanophenol → HCID 18650838, compound

HRID 1589764Notes

Reaction equation

HRID 1589764 reaction equation
[Cl:1][C@@H:2]([CH3:22])[CH2:3][C@H:4]([CH3:21])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[C:23]([C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1)#[N:24].N1(C2C=CN=CC=2)CCCC1>C(Cl)Cl>[C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:17][C:16](=[O:18])[C:15]2[CH:19]=[CH:20][C:12]([C:9]3[CH:8]=[CH:7][C:6]([O:5][C@@H:4]([CH3:21])[CH2:3][C@@H:2]([Cl:1])[CH3:22])=[CH:11][CH:10]=3)=[CH:13][CH:14]=2)=[CH:27][CH:26]=1)#[N:24]

Participants

5

Reactant 3

HCID 130194-CyanophenolHCID 755674-PyrrolidinopyridineHCID 18650841HCID 18650841, compound

Product 1

HCID 18650838HCID 18650838, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl (R,S)-4-[4'-(3"-hydroxy-1"-methylbutoxy)-phenyl]benzoate, which had been obtained from methyl 4(4'-hydroxyphenyl)benzoate and monotosylate of (R,R)-2,4-pentadiol, was chlorinated and hydrolyzed. 0.5 g of the (S,S)-4-[4'-(3"-chloro-1"-methylbutoxy)phenyl]-benzoic acid thus obtained, 0.19 g of 4-cyanophenol, 0.04 g of 4-pyrrolidinopyridine, 0.34 g of dicycylohexylcarbodiimide and 6 ml of methylene chloride were stirred at room temperature for five hours. The dicyclohexyl urea thus precipitated was filtered and the filtrate was desolvated. The obtained crude product was recrystallized from ethyl alcohol to thereby give 0.4 g of the title compound (m.p.: 103.8° C.).

Workup

  1. customThe dicyclohexyl urea thus precipitated
  2. filtrationwas filtered
  3. customThe obtained crude product
  4. customwas recrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-a640d39ed7f34c45bb84aa6e06e82cec
Source dataset
uspto-grants-1993_04
Patent number
US05200111

Reaction notes

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