Water → HCID 54027108, compound

HRID 568753Notes

Reaction equation

HRID 568753 reaction equation
[CH3:1][CH:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:17]([O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>N1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:1][CH:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:29](=[O:30])[C:28]2[CH:27]=[CH:26][C:25]([O:24][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:33][CH:32]=2)=[CH:12][CH:11]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 962WaterHCID 37664104-Benzyloxybenzoylchloride2×HCID 13741970HCID 13741970, compound

Product 1

HCID 54027108HCID 54027108, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent2×

Procedure

Optically active p-(1-methyl-heptyloxy)phenol (50.0 g, 0.22 mol) was dissolved in pyridine (300 ml), followed by dropwise adding to the solution, a solution of p-benzyloxybenzoic acid chloride (50.0 g, 0.20 mol) prepared above in (ii), dissolved in toluene (300 ml), under ice cooling, agitating the mixture for 2 hours while keeping it at about 50°~60° C., allowing it to stand overnight, thereafter adding toluene (1,500 ml) and water (1,000 ml), agitating the mixture, washing the toluene layer with 6N-HCl, then with 2N-NaOH aqueous solution and further with water until the wash water became neutral, distilling off toluene, and recrystallizing the residue from ethanol to obtain optically active p-benzyloxybenzoic acid p-(1-methyl-heptyloxy)phenyl ester (69.0 g).

Workup

  1. additionby dropwise adding to the solution
  2. customat about 50°~60° C.
  3. waitto stand overnight
  4. washwashing the toluene layer with 6N-HCl
  5. distillationdistilling off toluene
  6. customrecrystallizing the residue from ethanol

Sources & evidence

ORD record
ord-b3984006ae674705b6fe92cf7b0081e3
Source dataset
uspto-grants-1988_03
Patent number
US04729847

Reaction notes

Loading…