Methanol → 2-(4-(Tert-butoxycarbonyl)phenyl)acetic acid

HRID 1013511Notes

Reaction equation

HRID 1013511 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].CO.[OH-].[Na+]>C1COCC1>[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

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57541233Dimethyl [4-(tert-butoxycarbonyl)phenyl]malonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl [4-(tert-butoxycarbonyl)phenyl]malonate (4.00 g, 13.0 mmol) was taken up in THF (30 mL) and MeOH (10 mL) under N2. NaOH (2 M, 19.5 mL, 39.0 mmol) was added, and the reaction was stirred at room temperature for 45 min. The solution was quenched with 1 M citric acid and extracted with EtOAc (2×). The combined organic extracts were washed with water and brine, dried (MgSO4), and evaporated. The resulting yellow oil was dissolved in 1:1 EtOAc:water (100 mL) and stirred at 85° C. for 2 h. The mixture was diluted with 1 M citric acid and extracted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4), and evaporated to give [4-(tert-Butoxycarbonyl)phenyl]acetic acid as a tan solid. 1H NMR (DMSO-d6, 600 MHz) δ 12.42 (bs, 1H), 7.82 (d, J=8.3 Hz, 2H), 7.35 (d, J=8.3 Hz, 2H), 3.64 (s, 2H), 1.51 (s, 9H). MS: cal'd 259 (MNa+), exp 259 (MNa+).

Workup

  1. customThe solution was quenched with 1 M citric acid
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. dissolutionThe resulting yellow oil was dissolved in 1:1 EtOAc
  7. stirringwater (100 mL) and stirred at 85° C. for 2 h
  8. additionThe mixture was diluted with 1 M citric acid
  9. extractionextracted with EtOAc
  10. washThe organic layer was washed with water and brine
  11. dry with materialdried (MgSO4)
  12. customevaporated

Sources & evidence

ORD record
ord-edba07e3fa584adcbb55232d170001c9
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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