Potassium Carbonate → Methyl 2-[(4-nitronaphthalen-1-yl)oxy]acetate

HRID 1641269Notes

Reaction equation

HRID 1641269 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24]>CN1CCCC1.O>[CH3:26][O:25][C:23](=[O:24])[CH2:22][O:14][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 3438294-Nitro-1-naphthol

Product 1

HCID 59553182Methyl 2-[(4-nitronaphthalen-1-yl)oxy]acetateYield 325.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 84541-MethylpyrrolidineSolvent

Conditions

Temperature
70 °C

Procedure

4-Nitronaphthalen-1-ol (0.70 g, 3.7 mmol) in N-methylpyrrolidine (6 ml) is treated with potassium carbonate (1.0 g) and methyl bromoacetate (0.169 g, 1.1 eq). The mixture is stirred at 70° C. for 5 h. The mixture is then diluted with water and extracted with ethyl acetate. The organic layer is repeatedly washed with water, dried over Na2SO4, and evaporated to dryness to provide (4-nitronaphthalen-1-yloxy)-acetic acid methyl ester (0.94 g). MS: 262 (M+1).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is repeatedly washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-6443a6905a9d496a945c558353d5ccd9
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

Loading…