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

HRID 401177Notes

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-076eb4ef24bc4c088771d19e4a9f391c
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741915B2

Reaction notes

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