Toluene → 4-(Benzyloxy)phenyl 4-(decyloxy)benzoate

HRID 1090608Notes

Reaction equation

HRID 1090608 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C1(C)C=CC=CC=1.C(Cl)Cl>CCOCC.C(N(CC)CC)C>[CH2:16]([O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([O:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:14][CH:13]=2)=[O:32])=[CH:29][CH:28]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6344DichloromethaneHCID 7638MonobenzoneHCID 117793534-Decyloxybenzoyl chloride

Product 1

HCID 199134434-(Benzyloxy)phenyl 4-(decyloxy)benzoateYield 95.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

4-Benzyloxyphenol (20.0 g. 100 mmol) was dissolved in 200 mL dry ether and 10 mL triethylamine. 4-Decyloxybenzoyl chloride (30.0 g, 100 mmol) was added dropwise with stirring at room temperature under nitrogen. After 1 day of stirring at room temperature under nitrogen atmosphere, 200 mL toluene and 200 mL methylene chloride were added to the reaction mixture. The reaction mixture was then filtered and the filtrate washed twice with 0.5N HCl, once with water, and dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was recrystallized from toluene-ethanol to provide 43.9 g (95% yield) 4-benzyloxyphenyl 4-decyloxybenzoate.

Workup

  1. stirringAfter 1 day of stirring at room temperature under nitrogen atmosphere
  2. filtrationThe reaction mixture was then filtered
  3. washthe filtrate washed twice with 0.5N HCl, once with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was recrystallized from toluene-ethanol

Sources & evidence

ORD record
ord-914f96f867904f4f853a847747301ff4
Source dataset
uspto-grants-1992_01
Patent number
US05082587

Reaction notes

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