4-Chlororesorcinol → HCID 13246701, compound

HRID 2412304Notes

Reaction equation

HRID 2412304 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1[OH:9].[Cl:10][C:11]1([Cl:16])[CH2:13][CH:12]1[CH2:14]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1[O:9][CH2:14][CH:12]1[CH2:13][C:11]1([Cl:16])[Cl:10].[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([O:6][CH2:14][CH:12]2[CH2:13][C:11]2([Cl:16])[Cl:10])=[CH:4][C:3]=1[OH:9]

Participants

7

Reactant 4

HCID 17314-ChlororesorcinolHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 47395822-BROMOMETHYL-1 1-DICHLOROCYCLOPROPANE

Product 2

HCID 13246701HCID 13246701, compoundHCID 13368146HCID 13368146, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

In 700 ml of N,N-dimethylformamide, there was dissolved 181 g of 4-chlororesorcinol. To the solution, there were added 283 g of (2,2-dichlorocyclopropyl)methyl bromide, 207 g of anhydrous potassium carbonate and 4 g of sodium iodide. The mixture was stirred at 90° C. for 15 hours, then poured into ice water and extracted with diethyl ether. The ether layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was then distilled off. The oily residue was subjected to preparatory high-speed liquid chromatography to give 93 g of 4-chloro-3-[(2,2-dichlorocyclopropyl)methoxy]phenol and 5 g of 2-chloro-5-[(2,2-dichlorocyclopropyl)methoxy]phenol.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was then distilled off

Sources & evidence

ORD record
ord-48ea252fc729446b89f5c716e9ac2a6a
Source dataset
uspto-grants-1985_01
Patent number
US04491465

Reaction notes

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