Iodoethane → HCID 23136282, compound

HRID 1909863Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 3-hydroxy-4-methyl benzoic acid (3.0 g), potassium carbonate (10.9 g), and acetonitrile (60 mL) was added ethyl iodide (4.8 mL) under ice-cooling, followed by stirring at 60° C. overnight. Thereafter, ethyl iodide (4.8 mL) was added thereto, followed by stirring at 70° C. for 3 days. In addition, ethyl iodide (4.8 mL) and potassium carbonate (5.5 g) were added thereto, followed by stirring overnight. To the reaction mixture was added water (100 mL), followed by extraction with ethyl acetate, and the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane:5/95) to obtain ethyl 3-ethoxy-4-methylbenzoate (4.0 g).

Workup

temperaturecooling
stirringby stirring at 70° C. for 3 days
stirringby stirring overnight
extractionfollowed by extraction with ethyl acetate
washthe obtained organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane:5/95)

Sources & evidence

ORD record: ord-197d300a8d464c5a8dd74eb9d0cc1f58
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598355B2

Reaction notes

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