Sodium Hydroxide → 2-(4-(Tert-butoxycarbonyl)phenyl)acetic acid

HRID 1919914Notes

Reaction equation

HRID 1919914 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH:14](C(OC)=O)[C:15]([O:17]C)=[O:16])=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:1]([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 57541233Dimethyl [4-(tert-butoxycarbonyl)phenyl]malonate

Product 1

HCID 598545182-(4-(Tert-butoxycarbonyl)phenyl)acetic acid

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl [4-(tert-butoxycarbonyl)phenyl]malonate (4.00 g, 13.0 mmol) in THF (30 mL) and MeOH (10 mL) was added NaOH (2N, 19.5 mL, 38.9 mmol). After stirring the reaction for 45 minutes at room temperature, it was diluted with 1 M citric acid and extracted with EtOAc. The organic layer was washed (water, brine), dried (MgSO4), and concentrated to a yellow residue. The residue was redissolved in EtOAc (50 mL) and H2O (50 mL) and stirred for 2 h at 80° C. The mixture was extracted with EtOAc, washed with water and brine, dried (MgSO4), and concentrated to give [4-tert-butoxycarbonyl)phenyl]acetic acid as an off-white solid. MS (ESI) calcd [M+Na]+ 259.1, found 259.1.

Workup

  1. customthe reaction for 45 minutes at room temperature
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed (water, brine)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to a yellow residue
  6. dissolutionThe residue was redissolved in EtOAc (50 mL)
  7. stirringH2O (50 mL) and stirred for 2 h at 80° C
  8. extractionThe mixture was extracted with EtOAc
  9. washwashed with water and brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated
  12. customto give [4-tert-butoxycarbonyl)phenyl]acetic acid as an off-white solid

Sources & evidence

ORD record
ord-4277a044ce0342958d6002a7a00e4a83
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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