Lithium hydroxide, monohydrate → 3-[4-(Benzyloxy)phenyl]-2-ethoxypropanoic acid

HRID 987274Notes

Reaction equation

HRID 987274 reaction equation
O.[OH-].[Li+].C([O:6][C:7](=[O:27])[CH:8]([O:24][CH2:25][CH3:26])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)C>O.O1CCOCC1>[CH2:17]([O:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][CH:8]([O:24][CH2:25][CH3:26])[C:7]([OH:27])=[O:6])=[CH:15][CH:14]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 110779683-(4-Benzyloxyphenyl)-2-ethoxypropanoic acid ethyl ester

Product 1

HCID 109245703-[4-(Benzyloxy)phenyl]-2-ethoxypropanoic acidYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Lithium hydroxide hydrate (7.4 g; 177 mmole) dissolved in water (150 ml) was added to a solution of 3-(4-benzyloxyphenyl)-2-ethoxypropanoic acid ethyl ester (23.25 g; 70.8 mmole) in dioxane (150 ml). After stirring at room temperature over night dioxane was evaporated in vacuo, water was added and the mixture was extracted with ethyl acetate. The water phase was acidified with hydrochloric acid (1 N) and extracted with ethyl acetate. The organic phase was washed with water and brine, dried and the solvent was evaporated in vacuo to give 21.1 g (yield 99.2%) of 3-(4-benzyloxyphenyl)-2-ethoxypropanoic acid.

Workup

  1. customwas evaporated in vacuo, water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water and brine
  6. customdried
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-9f946f29b81f4e1c9122cc02aae6639f
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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