4-Nitrobenzoic Acid → 1-Phenylethanol, (S)-

HRID 1162890Notes

Reaction equation

HRID 1162890 reaction equation
[C:1]1([C@@H:7]([OH:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:29]([C:32]1[CH:40]=[CH:39][C:35]([C:36](O)=[O:37])=[CH:34][CH:33]=1)([O-:31])=[O:30].COCCOC(N=NC(OCCOC)=O)=O>C1(C)C=CC=CC=1.O>[N+:29]([C:32]1[CH:33]=[CH:34][C:35]([C:36]([O:9][C@@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:8])=[O:37])=[CH:39][CH:40]=1)([O-:31])=[O:30].[C:1]1([C@@H:7]([OH:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 4431351-Phenylethanol, (S)-HCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamate

Product 2

HCID 4431351-Phenylethanol, (S)-HCID 7657150HCID 7657150, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

After (S)-1-phenylethyl alcohol (176 mg, 1.43 mmol), triphenylphosphine (449.8 mg, 1.72 mmol), 4-nitrobenzoic acid (288 mg, 1.72 mmol), and toluene (7 ml) were added to a 50 ml flask, azodicarboxylic acid bis(2-methoxyethyl) ester (403 mg, 1.72 mmol) dissolved in toluene (3.5 ml) was added dropwise thereto at 20° C., and the reaction was allowed to proceed for 6 hours. Water (10 mL) was added, and separation was carried out. Then, the aqueous layer was extracted using toluene (10 mL,×1). The resulting organic layer was collectively washed with water (10 mL) and saturated salt water (10 ml), and dehumidified with anhydrous magnesium sulfate. Subsequently, a crude product obtained by concentration was purified by column chromatography (silica gel, 5% ethyl acetate-hexane solution) to give (R)-1-(4-nitrobenzoyloxy)-1-phenylethane as a pale yellow liquid substance (352 mg, yield: 91%/(S)-1-phenylethyl alcohol).

Workup

  1. additionwas added dropwise
  2. customat 20° C.
  3. customseparation
  4. extractionThen, the aqueous layer was extracted
  5. washThe resulting organic layer was collectively washed with water (10 mL) and saturated salt water (10 ml)
  6. customSubsequently, a crude product obtained by concentration
  7. customwas purified by column chromatography (silica gel, 5% ethyl acetate-hexane solution)

Sources & evidence

ORD record
ord-4d5e4331348f4022ad010a74278939fd
Source dataset
uspto-grants-2010_10
Patent number
US07820802B2

Reaction notes

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