Lithium Hydroxide → HCID 66648954, compound

HRID 1774381Notes

Reaction equation

HRID 1774381 reaction equation
[CH2:1]([CH:8]([C:24]([O:26]CC)=[O:25])[C:9]([OH:23])([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:10]([O:12]CC)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCOCC1.C(OCC)(=O)C>[CH2:1]([CH:8]([C:24]([OH:26])=[O:25])[C:9]([OH:23])([CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66648766HCID 66648766, compound

Product 1

HCID 66648954HCID 66648954, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a diethyl 3-benzyl-2-hydroxy-2-phenethylsuccinate (806 mg, 2.1 mmol) in 1,4-dioxane (8.0 mL) was added 1 M aqueous lithium hydroxide solution (8.4 mL, 8.4 mmol) at room temperature, and the mixture was stirred at 60° C. for 48 h. The reaction mixture was quenched and adjusted to pH 1 with 1 M hydrochloric acid with stirring under ice cooling. The solvent was evaporated under reduced pressure, and the residue thus obtained was dissolved in ethyl acetate, and washed with water and brine. The organic layer was concentrated under reduced pressure and dried in vacuum to give 651 mg (crude) of 3-benzyl-2-hydroxy-2-phenethylsuccinic acid

Workup

  1. customThe reaction mixture was quenched
  2. stirringwith stirring under ice cooling
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue thus obtained
  5. washwashed with water and brine
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customdried in vacuum

Sources & evidence

ORD record
ord-4b31896910884f2b908f423bac681c67
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

Loading…