Iodoethane → HCID 14745488, compound

HRID 1199241Notes

Reaction equation

[Cl:1][C:2]1[C:10]([OH:11])=[C:9]([S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:17](I)[CH3:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:17]([O:11][C:10]1[C:2]([Cl:1])=[C:3]([CH:7]=[CH:8][C:9]=1[S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])[C:4]([OH:6])=[O:5])[CH3:18]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of the 2-chloro-4-ethylsulfonyl-3-hydroxybenzoic acid prepared in Example 4 (0.075 mole), ethyl iodide (0.5 mole), and potassium carbonate (0.1 mole) in dimethylformamide (150 ml) was heated at 90° C. for 7 hours. After cooling, the reaction mixture was partitioned between ethyl acetate and 5% potassium carbonate. The ethyl acetate layer was then washed with brine, dried over magnesium sulfate, and concentrated in vacuo to afford the crude ethyl ester of the desired benzoic acid. Hydrolysis of the ester to the acid was accomplished by stirring the ester (0.075 mole) with a base such as sodium hydroxide (0.1 mole) in ethanol (100 ml) at room temperature for 16 hours. The reaction mixture was acidified with 2N HCl, and then partitioned between methylene chloride and water. The methylene chloride layer was dried over magnesium sulfate and concentrated in vacuo to afford the acid as an oil.

Workup

temperatureAfter cooling
customthe reaction mixture was partitioned between ethyl acetate and 5% potassium carbonate
washThe ethyl acetate layer was then washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d30570bec62f4cd2baca81c2c0162a11
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04898973

Reaction notes

Loading…