Hydrochloric Acid → 2-(4-Chloro-2-nitrophenyl)ethanol

HRID 1743868Notes

Reaction equation

HRID 1743868 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH2:12]=[O:13].O.Cl>CS(C)=O.C(O)C.[OH-].[K+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:12][OH:13])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 962WaterHCID 6975Benzene, 4-chloro-1-methyl-2-nitro-

Product 1

HCID 144915122-(4-Chloro-2-nitrophenyl)ethanolYield 62.5%

Reagents, catalysts & solvents 3

HCID 14797Potassium HydroxideCatalystHCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

To a solution of 4-chloro-1-methyl-2-nitro-benzene (171.6 g, 0.5 mole) in DMSO (150 mL) was added paraformaldehyde (30.0 g, 1.0 mole), followed by potassium hydroxide (1.5 g, 0.027 mol) in ethanol (10 mL). The resulting reaction mixture was stirred at room temperature for six days and water (2 L) was added and the mixture neutralized with hydrochloric acid (2 N). The mixture was extracted with ethyl ether (2×1 L) and the combined organic layers were washed with water (1 L), saturated sodium chloride (1 L), dried (sodium sulfate) and concentrated to a yellow solid. Purification by flash column chromatography (silica gel, methylene chloride:hexanes 1:2) provided 63.0 g of the title compound as a yellow solid. 1H NMR (DMSO-d6): 7.90 δ (s, 1H); 7.50 δ (d, 1H); 7.36 δ (d, 1H); 3.90 δ (t, 2H); 3.15 δ (t, 2H); 1.50 δ (broad, 1H).

Workup

  1. customThe resulting reaction mixture
  2. extractionThe mixture was extracted with ethyl ether (2×1 L)
  3. washthe combined organic layers were washed with water (1 L), saturated sodium chloride (1 L)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated to a yellow solid
  6. customPurification by flash column chromatography (silica gel, methylene chloride:hexanes 1:2)

Sources & evidence

ORD record
ord-a3d0a232cf574efb97507d34f285c393
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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