Toluene → 2-Methylbutyl 4-[p-(7-octenyloxy)benzoyloxy]biphenyl-4-carboxylate

HRID 1612583

Reaction equation

HRID 1612583 reaction equation
C1(C)C=CC=CC=1.O[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23][CH2:24][CH:25]([CH3:28])[CH2:26][CH3:27])=[O:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.[CH2:29]([O:37][C:38]1[CH:46]=[CH:45][C:41]([C:42]([OH:44])=[O:43])=[CH:40][CH:39]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH2:36]>N1C=CC=CC=1>[CH2:29]([O:37][C:38]1[CH:39]=[CH:40][C:41]([C:42]([O:44][C:18]2([C:21]([O:23][CH2:24][CH:25]([CH3:28])[CH2:26][CH3:27])=[O:22])[CH:19]=[CH:20][C:15]([C:12]3[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=3)=[CH:16][CH2:17]2)=[O:43])=[CH:45][CH:46]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH2:36]

Participants

5

Reactant 3

HCID 1140TolueneHCID 139075372-Methylbutyl 4'-hydroxybiphenyl-4-carboxylateHCID 139976794-(7-Octenyloxy)benzoic acid

Product 1

HCID 675687822-Methylbutyl 4-[p-(7-octenyloxy)benzoyloxy]biphenyl-4-carboxylateYield 45%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A toluene solution containing 10 g of 2-methylbutyl 4'-hydroxybiphenyl-4-carboxylate and 3 g of pyridine was added dropwise to the above-described toluene solution of the acid chloride compound. After conclusion of dropping, the temperature was raised, and reaction was carried out for 8 hours at 50° C. After conclusion of the reaction, the product was washed with water and dried over magnesium sulfate, and the dried product was concentrated under reduced pressure. The residue was recrystallized from ethanol to obtain 8.2 g of the objective ester compound. (Yield: 45%)

Workup

  1. temperaturethe temperature was raised
  2. customreaction
  3. customAfter conclusion of the reaction
  4. washthe product was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationthe dried product was concentrated under reduced pressure
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-feb8f3b16bb84ea5a904ba6159610c36
Source dataset
uspto-grants-1993_03
Patent number
US05190686

Linked notes

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