Acetonitrile → 3-(4-Carboxymethylbenzyloxy)benzamide

HRID 850047Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].[C:11](=[O:14])([O-])[O-:12].[K+].[K+].Cl[C:18]1[CH:27]=[CH:26][C:21]([C:22](OC)=O)=[C:20](C)[CH:19]=1.[C:29](#N)C>>[C:11]([CH2:29][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][O:1][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:7])=[O:6])=[CH:26][CH:27]=1)([OH:12])=[O:14]

Participants

Reactant 4

HCID 6342Acetonitrile

HCID 11430Potassium Carbonate

HCID 3424033-Hydroxybenzamide

HCID 22349978Methyl 4-Chloro-2-methylbenzoate

Product 1

HCID 183546083-(4-Carboxymethylbenzyloxy)benzamide

Procedure

To 3-hydroxybenzamide (1.37 g; 10 mmol) was added potassium carbonate (1.38 g; 10 mmol) and methyl 4-chloro-methylbenzoate (1.84 g; 10 mmol) in anhydrous acetonitrile (50 ml). The mixture was heated under reflux for 5 hours.

Workup

temperatureThe mixture was heated
temperatureunder reflux for 5 hours

Sources & evidence

ORD record: ord-c70d4bd5b17a40f6af95375e3ddffaeb
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06015827

Reaction notes

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