3'-Hydroxyphenylacetic acid → (3-{[2-(Methoxycarbonyl)benzyl]oxy}phenyl)acetic acid

HRID 2111972Notes

Reaction equation

HRID 2111972 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23]Br>C(O)C>[CH3:14][O:15][C:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][O:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1)=[O:25]

Participants

5

Reactant 3

HCID 121223'-Hydroxyphenylacetic acidHCID 14797Potassium HydroxideHCID 2734813Methyl 2-(bromomethyl)benzoate

Product 1

HCID 68872970(3-{[2-(Methoxycarbonyl)benzyl]oxy}phenyl)acetic acidYield 14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Hydroxyphenylacetic acid (760 mg, (5 mmol) was dissolved in ethanol (99.5%, 20 ml). Potassium hydroxide (560 mg, 10 mmol) was added. The mixture was stirred for 30 minutes. 2-Bromomethylbenzoic acid methyl ester (1.144 g, 5 mmol) was then dropped in. The resulting mixture was heated to reflux for 2 hours and then evaporated in vacuum to dry. Water and ethyl acetate were added into the residue and the phases were separated. The water phase was acidified with 10% hydrochloric acid, pH˜5, and then extracted with ethyl acetate. The organic phase was dried (magnesium sulphate) and evaporated in vacuum to dry. Chromatography of the residue on a column (ISOLUTE® SI, 5 g/25 ml) using DCM, MeOH/DCM (1:99) as eluant gave 213 mg, the desired product, yield 14%.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. customevaporated in vacuum
  4. customto dry
  5. additionWater and ethyl acetate were added into the residue
  6. customthe phases were separated
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic phase was dried (magnesium sulphate)
  9. customevaporated in vacuum
  10. customto dry
  11. customgave 213 mg

Sources & evidence

ORD record
ord-25c7f69e8dcb421ab4fdc3cdd92a5459
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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