Benzoic Acid → Methyl Benzoate

HRID 2049495Notes

Reaction equation

HRID 2049495 reaction equation
[OH-].[K+].N([CH2:5]NCNC(=O)OC(C)C)=O.[N+](=C)=[N-].[C:18]([OH:26])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)COCCO.O.CCOCC>[C:18]([O:26][CH3:5])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 243Benzoic AcidHCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 20345172HCID 20345172, compound

Product 1

HCID 7150Methyl BenzoateYield 81%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent8×HCID 8117Diethylene GlycolSolvent

Procedure

To a solution obtained by dissolving 4.2 g of potassium hydroxide in a mixed solvent of 15 ml of diethylene glycol (DEG) and 3 ml of water, 50 ml of ether was added. The temperature of a water bath was maintained at 45°-50° C. and when the ether began to be distilled out, a solution prepared by dissolving 8.8 g of isopropyl N-[(N-nitrosomethylamino)methyl]carbamate in 70 ml of ether was added dropwise thereto. The ether fraction rapidly changed to yellow. After adding dropwise for 15-20 minutes, ether was added dropwise in order to make the amount of ether in the flask constant. When about 70 ml of ether was added dropwise for 20 minutes, the distillate became colorless and the reaction was completed. To the distilled ether solution containing diazomethane, benzoic acid was added to produce methyl benzoate, and an excess of benzoic acid was back-titrated with 0.2 N NaOH. The amount of the diazomethane was 1.7 g (81% yield).

Workup

  1. customTo a solution obtained
  2. additionwas added
  3. temperatureThe temperature of a water bath was maintained at 45°-50° C.
  4. distillationto be distilled out
  5. customa solution prepared
  6. additionwas added dropwise
  7. additionAfter adding dropwise for 15-20 minutes
  8. additionwas added

Sources & evidence

ORD record
ord-88859811c00e47839b4ed7a24456640d
Source dataset
uspto-grants-1980_04
Patent number
US04197410

Reaction notes

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