Benzyl Alcohol → HCID 22033706, compound

HRID 1791881Notes

Reaction equation

HRID 1791881 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.O>CC1C=CC(C)=CC=1>[CH2:12]([C:7]1[CH:8]=[C:2]([C:1]([O:10][CH3:11])=[O:9])[C:3]([NH2:4])=[CH:5][CH:6]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 962WaterHCID 8635Methyl Anthranilate

Product 1

HCID 22033706HCID 22033706, compoundYield 4.4%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

Methyl anthranilate (30.9 g; 205 mmols) and benzyl alcohol (4.43 g; 40,9 mmols) were dissolved in 50 mL of p-xylene. Montmorillonite (1.3 g), activated with hydrochloric acid, was added to the reaction mixture, which was then heated to boiling. The water produced during the reaction was collected using a Dean-Starck-apparatus. After three hours the solvent and the excess of methyl anthranilate were distilled off at reduced pressure. Chromatography using silica gel 60 and heptane/ethyl acetate (19/1->9/1) as eluent afforded 430 mg (4.4%) of the desired methyl 5-benzylanthranilate.

Workup

  1. additionwas added to the reaction mixture, which
  2. temperaturewas then heated to boiling
  3. customwas collected
  4. distillationthe excess of methyl anthranilate were distilled off at reduced pressure

Sources & evidence

ORD record
ord-0c9f48fec2cb482d80d9f2140cec9bbb
Source dataset
uspto-grants-2006_07
Patent number
US07074831B2

Reaction notes

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