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

HRID 924966Notes

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-c7d1e2c07b774c99a9e38e8a068dc098
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09283229B2

Reaction notes

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