Sodium Hydroxide → Benzoic Acid

HRID 378580Notes

Reaction equation

HRID 378580 reaction equation
N1CCC([O:6][C:7](=[O:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)C1.[OH-].[Na+].C1O[C@H]1C1C=CC=CC=1>C1(C)C=CC=CC=1.O>[C:7]([OH:14])(=[O:6])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 114946(S)-styrene oxideHCID 9799108Pyrrolidin-3-yl Benzoate

Product 1

HCID 243Benzoic AcidYield 234.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

To a biphasic mixture of 25.0 gm of the compound of Example 2 (69 mmol, 1.0 equiv.) in 125 mL of toluene was added 2.75 gm of sodium hydroxide (69 mmol, 1.0 equiv.) dissolved in 20 mL of water followed by 8.27 gm (69 mmol, 1.0 equiv.) of (S)-styrene oxide. The reaction mixture was heated to reflux overnight, at which time HPLC analysis showed that only trace starting material remained. Upon cooling to room temperature the layers were separated. The organic layer was washed with an additional 1.4 gm (35 mmol, 0.5 equiv.) of sodium hydroxide dissolved in 20 mL of water followed by another wash with 20 mL of water. The toluene solvent was removed under vacuum to provide 19.77 gm (92%) of a thick oil which solidified on standing. The crude product contained an ~1.2:1.0 mixture of regioisomers and was used without further purification in the next step.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight, at which time HPLC analysis
  3. customwere separated
  4. washanother wash with 20 mL of water
  5. customThe toluene solvent was removed under vacuum

Sources & evidence

ORD record
ord-f41555957cce4c0fae9eb9c1d42e5a2e
Source dataset
uspto-grants-2000_02
Patent number
US06031114

Reaction notes

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