Water → 4-Benzyloxyphenylacetic acid

HRID 898658Notes

Reaction equation

HRID 898658 reaction equation
C(O[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][C:6]=1C)(=O)C.[O:20]1[CH2:24][CH2:23]CC1.[OH2:25].O.[OH-].[Li+]>CO>[CH2:12]([O:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:23][C:24]([OH:20])=[O:25])=[CH:10][CH:9]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 69215995HCID 69215995, compound2×

Product 1

HCID 810334-Benzyloxyphenylacetic acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl-4-benzyloxyphenyl acetate (Compound 16, 12.08 g, 47.2 mmol) in a mixture of methanol (45 mL), tetrahydrofuran (40 mL) and water (15 mL) was treated with lithium hydroxide monohydrate (5 g, 119 mmol) and the resulting reaction mixture was stirred at ambient temperature for 1 h. The precipitated solid in the reaction mixture was filtered and washed well with diethyl ether. The white solid was then dissolved in dilute, aqueous hydrochloric acid and the solution was extracted with ethyl acetate (×2). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a white solid (11 g, 96%).

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe precipitated solid in the reaction mixture was filtered
  3. washwashed well with diethyl ether
  4. dissolutionThe white solid was then dissolved
  5. additionin dilute
  6. extractionaqueous hydrochloric acid and the solution was extracted with ethyl acetate (×2)
  7. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-c92e6e5f4d11440bb304fa77a61b2e28
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

Loading…