Water → (4-Chloro-phenyl)-prop-2-ynyloxy-acetic acid

Temperature

50 °C

A mixture of potassium hydroxide (23.4 g, assay 90%) in propargyl alcohol (70 ml) is added to 4-chloro-benzaldehyde (7.2 g) and chloroform (13.4 g) in propargyl alcohol (10 ml) over 5 hours at 50° C. The reaction mixture is stirred at 50° C. for additional 3 hours. After cooling to room temperature water (150 ml) is added. The resulting mixture is extracted with tert butyl methyl ether (150 ml). The organic phase is again extracted with 4M potassium hydroxide (50 ml). The aqueous alkaline extracts are combined and made acidic (pH<3) by addition of concentrated hydrochloric acid. The aqueous phase is extracted with tert butyl methyl ether (2×150 ml). The organic phases are combined, extracted with water (1×100 ml), dried (magnesium sulfate) and evaporated. (4-Chloro-phenyl)-prop-2-ynyloxy-acetic acid (7.7 g) is obtained as oil, which solidifies on standing.

1. additionis added
2. extractionThe resulting mixture is extracted with tert butyl methyl ether (150 ml)
3. extractionThe organic phase is again extracted with 4M potassium hydroxide (50 ml)
4. additionby addition of concentrated hydrochloric acid
5. extractionThe aqueous phase is extracted with tert butyl methyl ether (2×150 ml)
6. extractionextracted with water (1×100 ml)
7. dry with materialdried (magnesium sulfate)
8. customevaporated

ORD record

ord-15c4126432ae483d9eaf7f604dbe9cf1

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129560B2