Hydrochloric Acid → HCID 66648453, compound

HRID 1774373Notes

Reaction equation

HRID 1774373 reaction equation
C([O:3][C:4](=[O:22])[C:5]([CH2:20][CH3:21])([OH:19])[CH:6]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]([O:9]CC)=[O:8])C.O.[OH-].[Na+].Cl>O1CCOCC1>[CH2:12]([CH:6]([C:7]([OH:9])=[O:8])[C:5]([CH2:20][CH3:21])([OH:19])[C:4]([OH:22])=[O:3])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 66648640HCID 66648640, compound

Product 1

HCID 66648453HCID 66648453, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

The 3-Benzyl-2-ethyl-2-hydroxysuccinic acid diethyl ester thus obtained was dissolved in 1,4-dioxane (5 mL), added with water (5 mL) and 5 M sodium hydroxide aqueous solution (15 mL), and stirred at 100° C. for 15 h. The reaction mixture was cooled to room temperature, adjusted to pH 1 with 1 M hydrochloric acid, and extracted with ethyl acetate. The organic layer having been washed with 1 M hydrochloric acid and brine was dried over anhydrous magnesium sulfate and then filtered. The organic layer was concentrated under reduced pressure to give 1.0 g (quantitative) of 3-benzyl-2-ethyl-2-hydroxysuccinic acid as a solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer having been washed with 1 M hydrochloric acid and brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-05ca32149ccc48aa8911a67fdcf6f8cd
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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