Water → tert-Butyl 4'-methyl[1,1'-biphenyl]-2-carboxylate

HRID 1645850Notes

Reaction equation

HRID 1645850 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([OH:16])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:23][C:24]([CH3:27])([O-])[CH3:25].[K+].O>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([O:16][C:24]([CH3:27])([CH3:25])[CH3:23])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 65578Oxalyl chlorideHCID 815682-(4-Methylphenyl)benzoic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 9838270tert-Butyl 4'-methyl[1,1'-biphenyl]-2-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

[Reference: European Patent Application 87-109919.8 example 85a, page 148 line 22]To a solution of 4'-methyl[1,1'-biphenyl]-2-carboxylic acid (25.0 g, 0.118 mol) in dichloromethane (120 mL) at 0° C. was added oxalyl chloride (2.0 M solution in methylene chloride (470 mL, 0.236 mol) over 30 minutes. The solution was warmed to 25° C., stirred for three hours and concentrated in vacuo to remove excess oxalyl chloride. The remaining residue was suspended in diethyl ether (300 mL), cooled to 0° C. and potassium t-butoxide (26.44 g, 0.236 mol) was added over 15 minutes keeping the temperature of the mixture between 15°-25° C. The mixture was allowed to warm to 25° C. and was stirred for one hour, poured into water (200 mL), and extracted with diethyl ether. The ether extract was then washed with aqueous sodium bicarbonate (saturated solution), dried (magnesium sulfate) and concentrated in vacuo to an amber oil. Subsequent distillation (124°-130° C., 0.6 mm Hg) yielded the title compound as a colorless liquid (27.7 g, 92%).

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove excess oxalyl chloride
  3. temperaturecooled to 0° C.
  4. custombetween 15°-25° C
  5. temperatureto warm to 25° C.
  6. stirringwas stirred for one hour
  7. extractionextracted with diethyl ether
  8. extractionThe ether extract
  9. washwas then washed with aqueous sodium bicarbonate (saturated solution)
  10. dry with materialdried (magnesium sulfate)
  11. concentrationconcentrated in vacuo to an amber oil
  12. distillationSubsequent distillation (124°-130° C., 0.6 mm Hg)

Sources & evidence

ORD record
ord-06daf5423cd74acb9b7bf2be8dbcce2a
Source dataset
uspto-grants-1993_01
Patent number
US05177097

Reaction notes

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