1-Butanol → Dibutyl biphenyl-4,4'-dicarboxylate

HRID 2373124

Reaction equation

HRID 2373124 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7]([OH:9])=[O:8])=[CH:3][CH:2]=1.[CH2:19](O)[CH2:20][CH2:21][CH3:22].[C:24]1(C)[CH:29]=CC=[CH:26][CH:25]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl.O>[C:1]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH2:29][CH2:24][CH2:25][CH3:26])=[O:17])=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7]([O:9][CH2:19][CH2:20][CH2:21][CH3:22])=[O:8])=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 2631-ButanolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 13084(1,1'-Biphenyl)-4,4'-dicarboxylic acid

Product 1

HCID 14962465Dibutyl biphenyl-4,4'-dicarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of biphenyl-4,4′-dicarboxylic acid (15.2 g, 63 mmol), 100 mL of n-butanol, 200 mL of toluene, and a catalytic amount of p-toluenesulfonic acid was heated at reflux with continuous separation of evolved water (Dean-Stark trap) for 7 d. The reaction mixture was cooled to ambient, diluted with dichloromethane, filtered, washed with 10% aqueous NaHCO3 then with brine, dried (MgSO4), and concentrated. The crude product was purified by recrystallization from heptane to obtain 13.4 g (60% of theory) of colorless crystals. 1H NMR (CDCl3): δ 0.97 (t, 6H), 1.5 (m, 4H), 1.8 (m, 4H), 4.35 (q, 4H), 7.68 (d, 4H), 8.13 (d, 4H).

Workup

  1. temperatureThe reaction mixture was cooled to ambient,
  2. filtrationfiltered
  3. washwashed with 10% aqueous NaHCO3
  4. dry with materialwith brine, dried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by recrystallization from heptane
  7. customto obtain 13.4 g (60% of theory) of colorless crystals

Sources & evidence

ORD record
ord-70ded966e2934b7c8ce1fa495d6fa081
Source dataset
uspto-grants-2008_12
Patent number
US07459263B2

Linked notes

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