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Water → 2-(4-Isopropoxy-3-methoxy-phenyl)-2-methyl-propionic acid

HRID 61814
Notes
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Reaction equation

HRID 61814 reaction equation
C([O:3][C:4](=[O:20])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]([CH3:17])[CH3:16])=[C:10]([O:18][CH3:19])[CH:9]=1)([CH3:7])[CH3:6])C.[OH-].[Na+].O>C1COCC1.CCO>[CH:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]([CH3:7])([CH3:6])[C:4]([OH:20])=[O:3])=[CH:9][C:10]=1[O:18][CH3:19])([CH3:16])[CH3:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 66834644HCID 66834644, compound

Product 1

HCID 668346712-(4-Isopropoxy-3-methoxy-phenyl)-2-methyl-propionic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028Tetrahydrofuran
Solvent

Conditions

Temperature
80 °C

Procedure

2-(4-Isopropoxy-3-methoxy-phenyl)-2-methyl-propionic acid ethyl ester (Compound L3-1, 1.45 g, 5.17 mmol) was dissolved in THF (13 mL) and EtOH (13 mL), added with 1 N aqueous solution of sodium hydroxide (10.3 mL, 2.0 eq.), and stirred at 80° C. overnight. The reaction solution was added to water and extracted with ethyl acetate. The aqueous layer was acidified by using 1 N aqueous solution of hydrochloric acid, extracted with ethyl acetate, washed with saturated brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the target compound (white solid, 1.10 g, 84%).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe drying agent was removed by filtration
  6. customthe residues obtained
  7. concentrationafter concentration under reduced pressure
  8. customwere purified by silica gel column chromatography (ethyl acetate/hexane)
  9. customto obtain the target compound (white solid, 1.10 g, 84%)

Sources & evidence

ORD record
ord-f865c7d0fe7f44da81d69c156db8f76c
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440922B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes