Hydrochloric Acid → 2-(3-Formylphenoxy)acetic acid

HRID 592074Notes

Reaction equation

HRID 592074 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][CH2:7][C:8]([O:10]CC)=[O:9])=[O:2].[OH-].[Na+].Cl>CO>[CH:1]([C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][CH2:7][C:8]([OH:10])=[O:9])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1494377Ethyl 2-(3-formylphenoxy)acetate2×

Product 1

HCID 6018952-(3-Formylphenoxy)acetic acidYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

ethyl 2-(3-formylphenoxy)acetate (47)/(1 eq) was taken in MeOH and cooled to 0° C. when NaOH (2 eq) solution was added drop wise. After completion of addition the reaction mixture was stirred at rt for 30 min. The reaction mixture was cooled to rt and acidified with dil HCl to attain pH 3 when a precipitate appeared which was filtered and washed well with water and dried well to yield a white solid (49%). NMR: δ 4.754 (s, 1H), 7.23-7.27 (m, 1H), 7.349 (s, 1H), 7.449 (d, J=4.8 Hz, 2H), 9.938 (s, 1H), 13.07 (s, 1H).

Workup

  1. additionwas added drop wise
  2. additionAfter completion of addition the reaction mixture
  3. temperatureThe reaction mixture was cooled to rt
  4. filtrationwas filtered
  5. washwashed well with water
  6. customdried well

Sources & evidence

ORD record
ord-b522a77d248e4268900a203f34313901
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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