Benzyl Alcohol → Benzyl 3-aminobenzoate

HRID 1110200Notes

Reaction equation

HRID 1110200 reaction equation
C(O)C1C=CC=CC=1.[N+](C1C=C(C=CC=1)C(Cl)=O)([O-])=O.[N+:21]([C:24]1[CH:25]=[C:26]([CH:37]=[CH:38][CH:39]=1)[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])([O-])=O>CCOCC.C(O)C.[Pt]=O>[NH2:21][C:24]1[CH:25]=[C:26]([CH:37]=[CH:38][CH:39]=1)[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]

Participants

7

Reactant 3

HCID 244Benzyl AlcoholHCID 8495Benzoyl chloride, 3-nitro-HCID 957455HCID 957455, compound

Product 1

HCID 15428374Benzyl 3-aminobenzoate

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Benzyl alcohol (10 g, 92.6 mmole) was treated with a solution of m-nitrobenzoyl chloride (17.5 g, 94.5 mmole) in ether (50 ml) added dropwise. The mixture was stirred at room temperature for eighteen hours, then washed twice with aqueous sodium bicarbonate, dried over sodium sulfate, and filtered. The filtrate was evaporated to dryness in vacuo and the residue chromatographed on silica gel eluted with 1:1 CH2Cl2 :hexane. The product fractions were combined and evaporated to dryness in vacuo. A portion (5.2 g, 20.2 mmole) of the resulting benzyl m-nitrobenzoate was dissolved in ethanol and hydrogenated over platinum oxide (70 mg) at 50 psi of H2. The resulting mixture was filtered and evaporated to dryness in vacuo to give benzyl m-aminobenzoate.

Workup

  1. additionadded dropwise
  2. washwashed twice with aqueous sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness in vacuo
  6. customthe residue chromatographed on silica gel
  7. washeluted with 1:1 CH2Cl2
  8. customevaporated to dryness in vacuo
  9. filtrationThe resulting mixture was filtered
  10. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-8e6bad6a5b5146f089dbb4369940352e
Source dataset
uspto-grants-1994_06
Patent number
US05324726

Reaction notes

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