Water → 2-Isopropoxypropanoic acid
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[Na].Br[CH:3]([CH3:9])[C:4]([O:6]CC)=[O:5].O.[OH-].[Na+].[CH:13]([OH:16])([CH3:15])[CH3:14]>>[CH3:14][CH:13]([O:16][CH:3]([CH3:9])[C:4]([OH:6])=[O:5])[CH3:15][Na].Br[CH:3]([CH3:9])[C:4]([O:6]CC)=[O:5].O.[OH-].[Na+].[CH:13]([OH:16])([CH3:15])[CH3:14]>>[CH3:14][CH:13]([O:16][CH:3]([CH3:9])[C:4]([OH:6])=[O:5])[CH3:15]A 500 milliliter, 3-neck flask equipped with a magnetic stirrer, thermometer, addition funnel, condenser and nitrogen bubbler was charged with 250 milliliters of dry isopropyl alcohol. Sodium metal (7.1 grams, 0.31 mole) in small pieces was added and the solution was heated to reflux to complete the reaction. After cooling to 60° C., 54.3 grams (0.30 mole) of ethyl 2-bromopropionate in 50 milliliters of isopropanol was added dropwise over a 20 minute period, and then the solution was refluxed for 2 hours, and left standing overnight. One hundred fifty (150) milliliters of water and 13.0 grams of sodium hydroxide pellets were added and then the mixture was distilled at 90° C., then cooled in an ice bath and acidified to pH2 with concentrated hydrochloric acid. The oil phase which formed was extracted with 150 milliliters of dichloromethane, CH2Cl2, and the extract was dried over anhydrous magnesium sulfate, filtered and topped on a roto-vac at 70° C. to yield 27.8 grams of a pale yellow viscous liquid of 2-(1-methylethoxy)propanoic acid.
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