Phloroglucinol → HCID 18357800, compound

HRID 617387Notes

Reaction equation

HRID 617387 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-23b84859d7ed44589a0ac8e97c7f7393
Source dataset
uspto-grants-1999_09
Patent number
US05948819

Reaction notes

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