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

HRID 6322

Reaction equation

HRID 6322 reaction equation
C1(C)C=CC=CC=1.[CH2:8]([O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15].O[C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([O:41][CH2:42][CH:43]([CH3:46])[CH2:44][CH3:45])=[O:40])=[CH:35][CH:34]=2)=[CH:29][CH:28]=1>N1C=CC=CC=1>[CH2:8]([O:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([O:23][C:36]2([C:39]([O:41][CH2:42][CH:43]([CH3:46])[CH2:44][CH3:45])=[O:40])[CH:35]=[CH:34][C:33]([C:30]3[CH:31]=[CH:32][CH:27]=[CH:28][CH:29]=3)=[CH:38][CH2:37]2)=[O:22])=[CH:24][CH:25]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15]

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 139075372-Methylbutyl 4'-hydroxybiphenyl-4-carboxylateHCID 139976794-(7-Octenyloxy)benzoic acid2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

9 g of p-(7-octenyloxy)benzoic acid obtained in 15.(1) was suspended in toluene, and the suspension was cooled in an ice bath. Added dropwise thereto was 6 g of thionyl chloride. After conclusion of the dropping, the temperature was raised and reaction was carried out for 6 hours at 80° C. After conclusion of the reaction, the reaction solution was concentrated under reduced pressure, to obtain an acid chloride compound. Toluene was added to the acid chloride compound, and the resulting toluene solution was cooled in an ice bath. A toluene solution containing 10 g of 2-methylbutyl 4'-hydroxybiphenyl-4-carboxylate and 3 g of pyridine was added dropwise into 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, dried over magnesium sulfate, and 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. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-de7405e7ac6843299a46eac854633c2b
Source dataset
uspto-grants-1993_09
Patent number
US05248446

Linked notes

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