Hydrochloric Acid → Carbonic acid 4-nitro-phenyl ester (R)-1-phenyl-ethyl ester

HRID 2369188Notes

Reaction equation

HRID 2369188 reaction equation
[C:1]1([C@H:7]([OH:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.CC1CCCO1.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:24].Cl>O>[C:1]1([C@H:7]([O:9][C:23](=[O:24])[O:25][C:26]2[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73012-MethyltetrahydrofuranHCID 821294-Nitrophenyl chloroformateHCID 6375161-Phenylethanol, (R)-

Product 1

HCID 11108942Carbonic acid 4-nitro-phenyl ester (R)-1-phenyl-ethyl esterYield 98.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (R)-1-phenyl-ethanol (60.6 g, 0.496 mol), pyridine (42.5 mL, 0.526 mol) and 2-methyl-tetrahydrofuran (600 mL) was cooled to 0° C. and p-nitrophenyl chloroformate (100 g, 0.496 mol) was added over 15 min keeping the internal temperature below 5° C. The reaction mixture was warmed to room temperature and stirred for 2 h. To the reaction mixture was added 1.0 M HCl in water (300 mL). Layers were separated. The organic layer was washed with 1N HCl (300 mL) and brine (300 mL), filtered, concentrated to dryness by rotary evaporation, and dried under vacuum to give the title compound (140 g) as a clear yellow oil.

Workup

  1. customthe internal temperature below 5° C
  2. temperatureThe reaction mixture was warmed to room temperature
  3. customLayers were separated
  4. washThe organic layer was washed with 1N HCl (300 mL) and brine (300 mL)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness by rotary evaporation
  7. customdried under vacuum

Sources & evidence

ORD record
ord-5c10aefd8f144a4984d9c6056539d193
Source dataset
uspto-grants-2014_04
Patent number
US08703791B2

Reaction notes

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