Potassium Hydroxide → 2,4-Dibenzyloxyphenoxyacetic acid

HRID 322917Notes

Reaction equation

HRID 322917 reaction equation
[CH2:1]([O:8][C:9]1[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:19]=[CH:18][C:10]=1[O:11][CH2:12][C:13]([O:15]CC)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO>[CH2:1]([O:8][C:9]1[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:19]=[CH:18][C:10]=1[O:11][CH2:12][C:13]([OH:15])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 10763088Ethyl 2,4-dibenzyloxyphenoxyacetate

Product 1

HCID 107612692,4-Dibenzyloxyphenoxyacetic acidYield 21.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 2,4-dibenzyloxyphenoxyacetate (2 g), 10% w/v potassium hydroxide (10 mL) and methanol (50 mL) is stirred at ambient temperature for 1 hour. The reaction is concentrated in vacuo and acidified with 1 N HCL then extracted with ethyl acetate (2×100 mL). The organic layer is washed with water (2×100 mL), dried over magnesium sulphate, filtered and concentrated in vacuo to give a white powder. Recrystallisation from ethyl acetate/cyclohexane affords 2,4-dibenzyloxyphenoxyacetic acid (0.4 g) as a white solid, m.p. 72° C. [Elemental Analysis:- C, 72.4, H, 5.50% Calculated for C, 72.5H, 5.53%].

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe organic layer is washed with water (2×100 mL)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a white powder
  8. customRecrystallisation from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-d2d0648a253240418ad543e91342584d
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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