4-Nitrobenzoic Acid → (+)-2-Octanol

HRID 551745Notes

Reaction equation

HRID 551745 reaction equation
[CH3:1][C@H:2]([OH:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].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>ClCCl.O>[N+:29]([C:32]1[CH:33]=[CH:34][C:35]([C:36]([O:9][C@@H:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:1])=[O:37])=[CH:39][CH:40]=1)([O-:31])=[O:30].[CH3:1][C@H:2]([OH:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 2723888(+)-2-OctanolHCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamate

Product 2

HCID 2723888(+)-2-OctanolHCID 59520618(R)-2-(4-nitrobenzoyloxy)octane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

After (S)-2-octanol (300 mg, 2.30 mmol), triphenylphosphine (726 mg, 2.76 mmol), 4-nitrobenzoic acid (462 mg, 2.76 mmol), and dichloromethane (12 ml) were added to a 50 ml flask, azodicarboxylic acid bis(2-methoxyethyl) ester (648 mg, 2.76 mmol) dissolved in dichloromethane (6 ml) was added dropwise thereto at 20° C., and the reaction was allowed to proceed for 1.5 hours. Water (10 mL) was added, and separation was carried out. Then, the aqueous layer was extracted using dichloromethane (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)-2-(4-nitrobenzoyloxy)octane as a pale yellow liquid substance (572 mg, yield: 89%/(S)-2-octanol).

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-5f2e9afbe40f46bbbaa99e2e4762add6
Source dataset
uspto-grants-2011_05
Patent number
US07947816B2

Reaction notes

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