Hydrochloric Acid → 2-(Chloromethyl)-4-nitrophenol

HRID 24289

Reaction equation

HRID 24289 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[ClH:11].COC[O:15][CH3:16]>OS(O)(=O)=O>[Cl:11][CH2:7][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:16]=1[OH:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9804-NitrophenolHCID 8020Dimethoxymethane

Product 1

HCID 763052-(Chloromethyl)-4-nitrophenolYield 76%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
70 °C

Procedure

A 5-necked flask equipped with mechanical overhead stirrer, gas inlet tube, reflux condenser and a thermometer was charged with 4-nitrophenol (100 g, 0.72 mol). Concentrated HCl 932%, 1.3 L), conc. H2SO4 (98%, 10 mL) and formaldehyde dimethylacetal (152.4 g, 2 moles) were added and the mixture was heated to 70° C. Gaseous HCl was bubbled through the mixture for 4 hours. During this time a thick white precipitate formed. The suspension was cooled to 0° C., the precipitate was isolated by vacuum filtration and the yellow powder was dried over night under vacuum to give 108.76 g of slightly impure 2-chloromethyl-4-nitrophenol (about 76% yield).

Workup

  1. customA 5-necked flask equipped with mechanical overhead stirrer, gas inlet tube
  2. temperaturereflux condenser
  3. customGaseous HCl was bubbled through the mixture for 4 hours
  4. customDuring this time a thick white precipitate formed
  5. temperatureThe suspension was cooled to 0° C.
  6. customthe precipitate was isolated by vacuum filtration
  7. customthe yellow powder was dried over night under vacuum

Sources & evidence

ORD record
ord-60a582a1f67047778e5b4ab65a829ff1
Source dataset
uspto-grants-2005_02
Patent number
US06855833B2

Linked notes

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