Water → 2-[(Propan-2-yl)oxy]propanoic acid

HRID 1446949Notes

Reaction equation

HRID 1446949 reaction equation
[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]

Participants

6

Reactant 5

HCID 962WaterHCID 3776Isopropanol2×HCID 14798Sodium HydroxideHCID 79040Ethyl 2-bromopropionateHCID 5360545Sodium

Product 1

HCID 170469102-[(Propan-2-yl)oxy]propanoic acid

Conditions

Temperature
60 °C

Procedure

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.

Workup

  1. customA 500 milliliter, 3-neck flask equipped with a magnetic stirrer
  2. additionthermometer, addition funnel, condenser
  3. temperaturethe solution was heated
  4. temperatureto reflux
  5. customthe reaction
  6. temperaturethe solution was refluxed for 2 hours
  7. waitleft
  8. distillationthe mixture was distilled at 90° C.
  9. temperaturecooled in an ice bath
  10. customThe oil phase which formed
  11. extractionwas extracted with 150 milliliters of dichloromethane, CH2Cl2
  12. dry with materialthe extract was dried over anhydrous magnesium sulfate
  13. filtrationfiltered
  14. customtopped on a roto-vac at 70° C.

Sources & evidence

ORD record
ord-fa462b01d7df40fea969bb10bf7d15b0
Source dataset
uspto-grants-1982_02
Patent number
US04314842

Reaction notes

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