Methanol → Benzoic Acid

HRID 2073431Notes

Reaction equation

HRID 2073431 reaction equation
[OH-].[Na+].CO.FC(F)(F)C(CCCCCC)CCO[C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:12]=1>O>[C:15]([OH:17])(=[O:16])[C:14]1[CH:20]=[CH:21][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 19890428HCID 19890428, compound

Product 1

HCID 243Benzoic AcidYield 77.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

72 mg of sodium hydroxide was dissolved in 0.5 ml of water, followed by addition of 0.5 ml of methanol and 205 mg of ethyl p-(3-trifluoromethylnonyloxy)benzoate and 4 hours of stirring at 50° C. After the reaction, water was added, methanol was removed by distillation under a reduced pressure, and 2N-hydrochloric acid was added, followed by extration with diethyl ether. The ether solution was dried with sodium sulfate, and the solvent was distilled off to obtain 146 mg of optically active p-3-trifluoromethylnonyloxy)benzoic acid (yield: 77.2%).

Workup

  1. additionwas added
  2. custommethanol was removed by distillation under a reduced pressure, and 2N-hydrochloric acid
  3. additionwas added
  4. dry with materialThe ether solution was dried with sodium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-fa794414a32648b89ce2d5a35595c580
Source dataset
uspto-grants-1990_04
Patent number
US04917817

Reaction notes

Loading…