HCID 68106974, compound → HCID 68107212, compound

HRID 2364679Notes

Reaction equation

HRID 2364679 reaction equation
CC(=C)C[O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:8]([O:10][CH3:11])=[O:9]>ClCCl>[OH:4][C:5]1[C:6]([CH2:8][C:7]([CH3:12])=[CH2:6])=[C:7]([CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:8]([O:10][CH3:11])=[O:9]

Participants

3

Reactant 1

HCID 68106974HCID 68106974, compound

Product 1

HCID 68107212HCID 68107212, compoundYield 115%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 3-(2-methylallyloxy)-4-nitro-benzoate 4a (4.52 g, 18 mmol) was heated to 190° C. and stirred for 3 hours. The reaction mixture was cooled down to room temperature followed by the addition of 50 mL of dichloromethane. The reaction solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound methyl 3-hydroxy-2-(2-methylallyl)-4-nitro-benzoate 4b (2.60 g, yield: 57.7%) as a yellow oil.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9f97467c67744334aeeda8022bbf2a4e
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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