(2,5-DIMETHYL-PHENYLSULFANYL)-ACETIC ACID synthesis
- Product Name:(2,5-DIMETHYL-PHENYLSULFANYL)-ACETIC ACID
- CAS Number:15310-87-9
- Molecular formula:C10H12O2S
- Molecular Weight:196.27
Yield:15310-87-9 88%
Reaction Conditions:
Stage #1: 2,5-dimethylthiophenol;ethyl bromoacetatewith potassium hydroxide in ethanol; for 18 h;
Stage #2: with ethanol;water for 18 h;
Stage #3: with hydrogenchloride;water at 4; pH=1; for 18 h;
Steps:
58
Example 58 -- Preparation of (2,5-Dimethyl-phenylsulfanyI)-acetic acid (Compound 58); [151] To a 250 mL round bottom flask equipped with a magnetic stir bar was added 2,5- dimethylbenzenethiol (3.5 mL, 25.8 mmol), ethyl bromoacetate (4.32 mL, 25.9 mmol), and 100 mL ethanol. Potassium hydroxide (4.44 g, 79.1 mmol) was added and allowed reaction to mix under nitrogen atmosphere for 18 hours. Water (50 mL) was added and the reaction was allowed to stir for another 18 hours under nitrogen atmosphere. Ethanol was removed under reduced pressure. The remaining solution was diluted with water, acidified to pH 1 with aqueous IN hydrochloric acid, and sonicated to form solid precipitate. The solution was cooled to 4CC for 18 hours. Filtered to collect crude product and re-suspended in LON sodium hydroxide. Acidified solution with IN hydrochloric acid to pH 4.5 and sonicated to form a precipitate. Continued adding IN hydrochloric acid until pH 1. Solution was cooled to 40C for 2 - 3 hours. Product (4.44 g, 88%) was isolated by filtration as a gel, mp 73-740C. Found: C: 61.18 %, H: 6.34 %, S:16.26%; C10H]2O2S requires C: 61.2 %, H: 6.16 %, S: 16.34%; IH NMR (d-DMSO): (COOH, not visible due to water in sample); δ 7.09, d; IH (aryl H); δ 7.06, s, IH (aryl H); δ 6.91, dd, IH (aryl H); δ 3.75, s, 2H (CH2); δ 2.24, s, 6H (aryl-Crfe's).
References:
WO2008/14430,2008,A1 Location in patent:Page/Page column 57
19040-62-1
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