Acetic Acid → 4-Nitrobenzyl alcohol

HRID 541176Notes

Reaction equation

HRID 541176 reaction equation
C1(CC[CH:9]([OH:11])C)C=CC=CC=1.[CH2:12]1[CH:17]2C3[NH+:20]([O-:21])[CH:15]([CH2:16]2)[CH2:14][CH:13]1C3.C(O)(=[O:24])C.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[N+:20]([C:15]1[CH:14]=[CH:13][C:12]([CH2:9][OH:11])=[CH:17][CH:16]=1)([O-:21])=[O:24]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 613024-Phenyl-2-butanolHCID 5363146Diisopropyl azodicarboxylateHCID 1015366402-Oxido-2-azoniatricyclo[3.3.1.03,7]nonane

Product 1

HCID 692754-Nitrobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-phenylbutan-2-ol (97.7 mg, 0.651 mmol), Nor-AZADO (0.90 mg, 6.51 μmol, 1 mol %) and acetic acid (37 μl, 0.651 mmol) in dichloromethane (0.65 ml) was added with DIAD (128 μl, 0.651 mmol, 1 equivalent), and the mixture was stirred for 8 hours under reflux by heating. The reaction mixture was added with saturated aqueous sodium carbonate (2 ml), and the mixture was extracted with dichloromethane. The organic layer was dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the objective compound (95.1 mg; yield, 99%). The spectrum data were found to be the same as those obtained in Example 5, (b).

Workup

  1. temperatureunder reflux
  2. temperatureby heating
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. customto obtain
  8. customthe objective compound (95.1 mg; yield, 99%)

Sources & evidence

ORD record
ord-af520bb9f8f549c9882c0c15c23e1b05
Source dataset
uspto-grants-2014_10
Patent number
US08871981B2

Reaction notes

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