Pyridine → (-)-4-(Octyloxy)phenyl 4-(1-methoxyethyl)-benzoate

HRID 2050412Notes

Reaction equation

HRID 2050412 reaction equation
[CH3:1][O:2][CH:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)[CH3:4].C(Cl)(=O)C(Cl)=O.[CH2:20]([O:28][C:29]1[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][CH:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][C:32]2[CH:33]=[CH:34][C:29]([O:28][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:30][CH:31]=2)=[O:10])=[CH:7][CH:6]=1)[CH3:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 77412Phenol, 4-(octyloxy)-HCID 14473435(-)-4-(1-Methoxyethyl)benzoic acid

Product 1

HCID 14513154(-)-4-(Octyloxy)phenyl 4-(1-methoxyethyl)-benzoateYield 98.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

An acid chloride prepared from 1.80 g (10 mmol) of (-)-4-(1-methoxyethyl)benzoic acid and oxalyl chloride was added to a solution comprising 2.66 g (12 mmol) of 4-(octyloxy)phenol, 10 g of pyridine and 30 g of toluene at room temperature. The mixed solution was stirred at the same temperature for one hour and then at 40° C. -50° C. for 2 hours. The resulting reaction mixture was treated and purified according to Example 1 to obtain 3.78 g (98.5% yield) of (-)-4-(octyloxy)phenyl 4-(1-methoxyethyl)-benzoate. [α]D20 =-57.7° (c=1, CHCl3).

Workup

  1. waitat 40° C. -50° C. for 2 hours
  2. customThe resulting reaction mixture
  3. additionwas treated
  4. custompurified

Sources & evidence

ORD record
ord-37feb1625e1944d5bb9047138e8bf470
Source dataset
uspto-grants-1991_05
Patent number
US05013479

Reaction notes

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