Phloroglucinol → HCID 18357800, compound

HRID 427990Notes

Reaction equation

HRID 427990 reaction equation
Cl[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][O:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[CH3:22])[C:3]([O:5][CH3:6])=[O:4].[N:23]([O-:25])=[O:24].[Na+].C1(C=C(O)C=C(O)C=1)O.O>CN(C)C=O>[CH3:22][C:16]1[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:15]=1[O:14][CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH:2]([N+:23]([O-:25])=[O:24])[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 359PhloroglucinolHCID 962WaterHCID 18357785HCID 18357785, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 18357800HCID 18357800, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 2-chloro-2-[2-(2,5-dimethylphenoxymethyl)phenyl]acetate (0.35 g, 1.1 mmol), sodium nitrite (0.13 g, 1.9 mmol) and phloroglucinol (0.145 g, 1.1 mol) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 6 hours. Water was added to the mixture. The resulting mixture was extracted with ether, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (n-hexane/methylene chloride=1/1) to give the desired compound methyl 2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-nitroacetate (0.08 g, 22%) as an oil.

Workup

  1. extractionThe resulting mixture was extracted with ether
  2. washwashed successively with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by column chromatography on silica gel (n-hexane/methylene chloride=1/1)

Sources & evidence

ORD record
ord-0620e31aafb5449ba62d5fdeed634aee
Source dataset
uspto-grants-2001_11
Patent number
US06313150B1

Reaction notes

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