Potassium Carbonate → HCID 18462171, compound

HRID 369484Notes

Reaction equation

HRID 369484 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6].I[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[N+:12]([C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[O:1][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123801-IodooctaneHCID 294866Methyl 3-hydroxy-4-nitrobenzoate

Product 1

HCID 18462171HCID 18462171, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A slurry of methyl 3-hydroxy-4-nitrobenzoate (5.5 g, 0.028 mol), iodooctane (10.0 g, 0.042 mol) and potassium carbonate (20 g) in 100 mL DMF was stirred at 100° C. for 3 hours. The reaction mixture was cooled to room temperature, diluted with 500 mL H2O, then extracted with ether/ethyl acetate (9/1, 2×200 mL). The combined organic solution was washed with 400 mL H2O, dried over sodium sulfate, and concentrated to form methyl 4-nitro-3-octoxybenzoate as an off-white oil (8.7 g, 100%).

Workup

  1. extractionextracted with ether/ethyl acetate (9/1, 2×200 mL)
  2. washThe combined organic solution was washed with 400 mL H2O
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9877032966e04583881403784b349805
Source dataset
uspto-grants-2000_10
Patent number
US06137003

Reaction notes

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