Acetic Acid → (R)-2-(4-(Benzyloxy)-3-nitrophenyl)oxirane

HRID 30434Notes

Reaction equation

HRID 30434 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:18])[CH2:16]Cl)=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].CC(O)=O.O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[CH2:16][O:18]2)=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 234347181-(4-Benzyloxy-3-nitrophenyl)-2-chloroethanol

Product 1

HCID 10880191(R)-2-(4-(Benzyloxy)-3-nitrophenyl)oxirane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

151.8 g (0.49 mol) of 1-(4-benzyloxy-3-nitrophenyl)-2-chloroethanol was dissolved in THF (0.75 L) and treated dropwise with NaOH (4 mol/L, 182 mL, 0.73 mol). After 1 hour, AcOH (30 mL) was added followed by water (2.5 L). The mixture was cooled and the precipitated product was recovered by filtration and dried under vacuum at 65° C. Yield: 133.0 g (99.3%); mass spectroscopy: [M+H]+=272; m.p.=66° C.; e.e. 99.5%.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe precipitated product was recovered by filtration
  3. customdried under vacuum at 65° C

Sources & evidence

ORD record
ord-9c2b8a9d4e16458db3b64caa59ba5bac
Source dataset
uspto-grants-2008_09
Patent number
US07423146B2

Reaction notes

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