Hydrochloric Acid → HCID 13477628, compound

HRID 370853Notes

Reaction equation

HRID 370853 reaction equation
[H-].[Na+].[C:3]([C:6]1[CH:22]=[CH:21][C:9]([O:10][CH2:11][C:12]2[CH:13]=[C:14]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:16][CH:17]=2)=[CH:8][C:7]=1[OH:23])(=[O:5])[CH3:4].[H][H].I[CH3:27].Cl>O1CCCC1>[C:3]([C:6]1[CH:22]=[CH:21][C:9]([O:10][CH2:11][C:12]2[CH:13]=[C:14]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:16][CH:17]=2)=[CH:8][C:7]=1[O:23][CH3:27])(=[O:5])[CH3:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 13477606HCID 13477606, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13477628HCID 13477628, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a degreased suspension of sodium hydride (23 g) in tetrahydrofuran at ice temperature is slowly added (under nitrogen) a solution of 3-[(4-acetyl-3-hydroxyphenoxy)methyl]nitrobenzene (13.6 g, prepared as in Example 1A) in tetrahydrofuran (100 ml). When hydrogen evolution ceases, the mixture is allowed to warm to room temperature and is stirred for 2 hours. To this slurry is added iodomethane (6.7 g, neat) and the mixture is stirred 15 hours at room temperature. Another 6.7 g of iodomethane is then added and the mixture is refluxed 6 hours. After cooling to room temperature, the reaction mixture is poured into 10% HCl and extracted with ether. The extracts are washed with saturated brine, then dried over MgSO4 and concentrated. Recrystallization from acetone gives 9.1 g (64% yield) of product, m.p. 111°-114° C.

Workup

  1. stirringthe mixture is stirred 15 hours at room temperature
  2. temperaturethe mixture is refluxed 6 hours
  3. temperatureAfter cooling to room temperature
  4. extractionextracted with ether
  5. washThe extracts are washed with saturated brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customRecrystallization from acetone

Sources & evidence

ORD record
ord-42c5bab7e0224d168838a284ecb7d6de
Source dataset
uspto-grants-1985_07
Patent number
US04528392

Reaction notes

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