Sodium Hydroxide → HCID 18672357, compound

HRID 1058299Notes

Reaction equation

HRID 1058299 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10](/[CH:14]=[CH:15]/[C:16]([O:18]CC)=[O:17])[CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10](/[CH:14]=[CH:15]/[C:16]([OH:18])=[O:17])[CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86585772HCID 86585772, compound

Product 1

HCID 18672357HCID 18672357, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl (2E)-3-[3-(tert-butoxycarbonyl)phenyl]prop-2-enoate from the previous step (3.44 g, 12.4 mmol) in EtOH (30 mL), was added 1N NaOH (15 mL, 15 mmol) and the mixture was stirred for 2 hours. The reaction was concentrated under reduced pressure to ˜20 mL, acidified with 10% aqueous citric acid and extracted with 2×100 mL EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and the solvent removed under reduced pressure to give (2E)-3-[3-(tert-butoxycarbonyl)phenyl]prop-2-enoic acid as an oil which solidified on standing (3.1 g, 100%). HPLC RT=2.43 min, method B; 1H NMR, 400 MHz, CDCl3, 8.16, (s, 1H); 8.03 (d, J=8 Hz, 1H); 7.81, (d, J=16 Hz, 1H); 7.70, (d, J=8 Hz, 1H); 7.47 (t, J=8 Hz, 1H); 6.52 (d, J=16 Hz, 1H); 1.62 (s, 9H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure to ˜20 mL
  2. extractionextracted with 2×100 mL EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-9978d9a36c354f89a859ff46e777b47a
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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