4-Nitrobenzoic Acid → 4-Nitrobenzoic Acid

HRID 551725Notes

Reaction equation

HRID 551725 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C@@H:21]([OH:26])[CH2:22][C@H:23]([OH:25])[CH3:24].COCCOC(N=NC(OCCOC)=O)=O.[N+:43]([C:46]1[CH:54]=[CH:53][C:49]([C:50]([OH:52])=[O:51])=[CH:48][CH:47]=1)([O-:45])=[O:44]>C1COCC1.O>[N+:43]([C:46]1[CH:47]=[CH:48][C:49]([C:50]([O:25][C@@H:23]([CH3:24])[CH2:22][C@H:21]([OH:26])[CH3:20])=[O:51])=[CH:53][CH:54]=1)([O-:45])=[O:44].[N+:43]([C:46]1[CH:47]=[CH:48][C:49]([C:50]([OH:52])=[O:51])=[CH:53][CH:54]=1)([O-:45])=[O:44]

Participants

8

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 27236832,4-Pentanediol, (-)-HCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamate

Product 2

HCID 61084-Nitrobenzoic AcidHCID 16202546HCID 16202546, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

After triphenylphosphine (565 mg, 2.16 mmol), (2R,4R)-2,4-pentanediol (226 mg, 2.16 mmol), and THF (6 ml) were added to a 50 mL flask, azodicarboxylic acid bis(2-methoxyethyl) ester (505 mg, 2.16 mmol) dissolved in THF (6 mL) was added dropwise thereto at 20° C. Subsequently, 4-nitrobenzoic acid (300 mg, 1.80 mmol) dissolved in THF (6 mL) was added dropwise thereto at 20° C., and the reaction was allowed to proceed for one hour. Water (0.5 ml) was added, and concentration was carried out. Then, water (10 ml) was added to the solution, and extraction was carried out using diethyl ether (10 mL, ×2). Then, the organic layer was 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, 40% ethyl acetate-hexane solution) to give (4S,2R)-4-(4-nitrobenzoyloxy)pentane-2-ol as a pale yellow solid substance (358 mg, yield: 79%/4-nitrobenzoic acid).

Workup

  1. additionwas added dropwise
  2. customat 20° C
  3. additionwas added dropwise
  4. customat 20° C.
  5. concentrationconcentration
  6. additionThen, water (10 ml) was added to the solution, and extraction
  7. washThen, the organic layer was washed with water (10 ml) and saturated salt water (10 ml)
  8. customSubsequently, a crude product obtained by concentration
  9. customwas purified by column chromatography (silica gel, 40% ethyl acetate-hexane solution)

Sources & evidence

ORD record
ord-fca87d226e4e414eb6621145cf492031
Source dataset
uspto-grants-2011_05
Patent number
US07947816B2

Reaction notes

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