Benzylamine → Pentan-2-YL 4-hydroxybenzoate

HRID 1492348Notes

Reaction equation

HRID 1492348 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([O:13][CH:14]([CH3:18])[CH2:15][CH2:16][CH3:17])=[O:12])=[CH:7][CH:6]=1)(=O)C.C(N)C1C=CC=CC=1>C(O)C.C(Cl)(Cl)Cl>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([O:13][CH:14]([CH3:18])[CH2:15][CH2:16][CH3:17])=[O:12])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 189501354-Acetoxy-l-(1-methylbutyloxycarbonyl)benzene

Product 1

HCID 19365293Pentan-2-YL 4-hydroxybenzoateYield 96.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

Two grams of the crude compound (2) was dissolved in 50 ml of ethanol and 4 g of benzylamine was added dropwise. The mixture was stirred at room temperature for 4 hours, then diluted with 500 ml of chloroform, washed with dilute hydrochloric acid and water in this order, and dried with magnesium sulfate. After the solvent was evaporated, the residue was subjected to isolation and purification by silica gel column chromatography to obtain 1.6 g of a final compound.

Workup

  1. washwashed with dilute hydrochloric acid and water in this order
  2. dry with materialdried with magnesium sulfate
  3. customAfter the solvent was evaporated
  4. customthe residue was subjected to isolation and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-1d632962eec24eb9be4f8d0db8c50c8f
Source dataset
uspto-grants-1994_12
Patent number
US05374375

Reaction notes

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