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

HRID 279682Notes

Reaction equation

HRID 279682 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 washed with diethyl ether. The water phase was acidified with hydrochloric acid (1 M) and the crude product was extracted with ethyl acetate, washed with water and brine, dried and the solvent was evaporated in vacuo to give 21.1 g (yield 99.2%) of 3-(4benzyloxyphenyl)-2-ethoxypropanoic acid.

Workup

  1. customwas evaporated in vacuo, water
  2. additionwas added
  3. washthe mixture was washed with diethyl ether
  4. extractionthe crude product was extracted with ethyl acetate
  5. washwashed with water and brine
  6. customdried
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-c10d627ea2e94e96abc286ae22c511a0
Source dataset
uspto-grants-2002_03
Patent number
US06362360B1

Reaction notes

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