Acetone → Benzoic acid, 2-ethoxy-4-methyl-, ethyl ester

HRID 2178061Notes

Reaction equation

[OH:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:18](I)[CH3:19].[CH3:21][C:22](C)=O>>[CH2:21]([O:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:18][CH3:19])=[O:5])[CH3:22]

Participants

Reactant 4

HCID 180Acetone

HCID 57882-Hydroxy-p-toluic acid

HCID 6340Iodoethane

HCID 11430Potassium Carbonate

Product 1

HCID 11816602Benzoic acid, 2-ethoxy-4-methyl-, ethyl esterYield 85%

Procedure

To a mixture of 2-hydroxy-4-methylbenzoic acid (5.0 g, 32.9 mmol), K2CO3 (18.9 g, 136.6 mmol) and acetone (50 mL) was added ethyl iodide (41.0 g, 263.2 mmol). The mixture was stirred at room temperature for 3 days. After filtration, the organic layer was concentrated to afford ethyl 2-ethoxy-4-methylbenzoate as colorless oil (5.7 g, 85%), which was used directly for next step.

Workup

filtrationAfter filtration
concentrationthe organic layer was concentrated

Sources & evidence

ORD record: ord-c0473fbaf1864bcc85ee40a8df395f25
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067893B2

Reaction notes

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