Nitromethane → HCID 11086592, compound

HRID 1073755Notes

Reaction equation

HRID 1073755 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH:10]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:17]([CH3:20])([O-:19])=[O:18].[OH-].[Na+]>CO.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9](/[CH:10]=[CH:20]/[N+:17]([O-:19])=[O:18])[CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehyde

Product 1

HCID 11086592HCID 11086592, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 1.02 g (4.63 mmol) of 3-cyclopentoxy-4-methoxybenzaldehyde in 20 mL of methanol was added 0.3 mL (5.5 mmol) of nitromethane followed by 0.2 g (5.0 mmol) of sodium hydroxide in 5 mL of water in single portions. The mixture was stirred for 4 hours after which time the decomposing mixture was concentrated, diluted with 20 mL of water and acidified to pH 1 with concentrated hydrochloric acid. The aqueous solution was extracted with three, 10 mL portions of chloroform and the combined organic fractions were dried over magnesium sulfate and concentrated. Liquid chromatography of the crude mixture over 100 g of silica gel eluting with 5% ethyl acetate in hexane provided an analytically pure solid.

Workup

  1. concentrationwas concentrated
  2. additiondiluted with 20 mL of water
  3. extractionThe aqueous solution was extracted with three, 10 mL portions of chloroform
  4. dry with materialthe combined organic fractions were dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-937e3b8dba9d47ed8b4148c5eae801fd
Source dataset
uspto-grants-1990_11
Patent number
US04971959

Reaction notes

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