Guaiacol → Methyl 4-(2-methoxy-phenoxy)-3-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzoate

HRID 1738626Notes

Reaction equation

HRID 1738626 reaction equation
Cl[C:2]1[C:11]([O:12][CH2:13][CH2:14][O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:22]([O-:24])=[O:23].C(=O)([O-])[O-].[K+].[K+].[C:31]1([O:38][CH3:39])[C:32](=[CH:34][CH:35]=[CH:36][CH:37]=1)[OH:33]>CC(C)=O>[CH3:39][O:38][C:31]1[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=1[O:33][C:2]1[C:11]([O:12][CH2:13][CH2:14][O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:22]([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 11430Potassium CarbonateHCID 23288648Methyl 4-chloro-3-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzoate

Product 1

HCID 23288681Methyl 4-(2-methoxy-phenoxy)-3-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4.28 g of methyl 4-chloro-3-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzoate were dissolved in acetone (250 ml), treated at RT with 5.0 g of potassium carbonate, 1.93 of guaiacol and the mixture was heated at reflux for 20 hours. It was poured on to ice-water and extracted with ethyl acetate. The organic phase was washed 3 times with 5% sodium hydroxide solution, then with water, dried over sodium sulphate and finally concentrated on a rotary evaporator. The crude product (6 g) was flash chromatographed on silica gel with hexane/ether (1/1). here was thus obtained the desired methyl 4-(2-methoxy-phenoxy)-3-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzoate as a pale yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 20 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed 3 times with 5% sodium hydroxide solution
  5. dry with materialwith water, dried over sodium sulphate
  6. concentrationfinally concentrated on a rotary evaporator
  7. customchromatographed on silica gel with hexane/ether (1/1)

Sources & evidence

ORD record
ord-64d4d74695bd44529cab07dff92ab0b1
Source dataset
uspto-grants-1999_10
Patent number
US05962682

Reaction notes

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