2-Aminophenol → HCID 18979174, compound

HRID 2393173Notes

Reaction equation

HRID 2393173 reaction equation
[C:1]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O-:9])=O.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1O.B(O)(O)O.C1(C)C(C)=CC=CC=1>O>[O:9]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:7]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 58012-AminophenolHCID 7237O-XyleneHCID 7628Boric AcidHCID 7330447HCID 7330447, compound

Product 1

HCID 18979174HCID 18979174, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of monoethyl heptanedioate (9.41 g), o-aminophenol (5.46 g), boric acid (3.09 g), and xylene (100 ml) was refluxed with water being azeotropically removed for 16 hours. After cooling to room temperature, the insoluble matter was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=2:1) to provide ethyl 6-(benzoxazol-2-yl)hexanoate (10.1 g).

Workup

  1. customazeotropically removed for 16 hours
  2. filtrationthe insoluble matter was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=2:1)

Sources & evidence

ORD record
ord-7b69458883d84e4a8716212e1c4ee5ec
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

Loading…