Ethanol → HCID 57008954, compound

HRID 1460376Notes

Reaction equation

HRID 1460376 reaction equation
C(N[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:6]=1[OH:14])(=O)C.[OH-].[Na+].[CH2:17]([O:19][CH2:20][CH2:21]Br)[CH3:18].[CH2:23]([OH:25])[CH3:24]>>[CH2:17]([O:19][CH2:20][CH2:21][O:14][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]=1[C:23](=[O:25])[CH3:24])[CH3:18]

Participants

5

Reactant 4

HCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 611412-Bromoethyl ethyl etherHCID 12484292HCID 12484292, compound

Product 1

HCID 57008954HCID 57008954, compound

Procedure

1g of 2-acetylamino-3-nitrophenol was mixed with an aqueous solution of sodium hydroxide (0.21g of NaOH in 5ml H2O) with stirring. 5ml of ethanol was added to the deep red solution formed and then 0.64ml of 2-bromoethyl ethyl ether added and the reaction mixture stirred for 1 hour at room temperature and refluxed overnight. After cooling 5ml of 2M sodium hydroxide was added to the mixture to increase the pH to pH 12. Then extraction with 2×15ml of dichoromethane was carried out, the combined dichloromethane extracts dried over sodium sulphate, the solvent evaporated off and the product purified by recrystallisation from ethanol/hexane/dioxan to leave 1.0g of 2-acetyl-3-nitrophenyl (2-ethoxyethyl) ether as a fine yellow solid.

Workup

  1. customformed
  2. stirringthe reaction mixture stirred for 1 hour at room temperature
  3. temperaturerefluxed overnight
  4. additionwas added to the mixture
  5. temperatureto increase the pH to pH 12
  6. extractionThen extraction with 2×15ml of dichoromethane
  7. dry with materialthe combined dichloromethane extracts dried over sodium sulphate
  8. customthe solvent evaporated off
  9. customthe product purified by recrystallisation from ethanol/hexane/dioxan

Sources & evidence

ORD record
ord-eb67e566f5644e558cba8f3ea6bc3e3b
Source dataset
uspto-grants-1991_12
Patent number
US05071468

Reaction notes

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