Formaldehyde → HCID 59833399, compound

HRID 1666557Notes

Reaction equation

HRID 1666557 reaction equation
[Br: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]>CS(C)=O>[Br: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

4

Reactant 2

HCID 712FormaldehydeHCID 1235464-Bromo-2-nitrotoluene

Product 1

HCID 59833399HCID 59833399, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-bromo-1-methyl-2-nitro-benzene (f-1) (0.01134 mol) and paraformaldehyde (0.009 mol) in DMSO (5 ml) and Triton-B (035 ml) was stirred at 50° C. for 2 hours, then cooled to room temperature and purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98.5/1.5; 35-70 μm). The pure fractions were collected and the solvent was evaporated. Yield: 1.18 g of 2-(4-Bromo-2-nitro-phenyl)-ethanol (f-2) (42%).

Workup

  1. temperaturecooled to room temperature
  2. custompurified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98.5/1.5; 35-70 μm)
  3. customThe pure fractions were collected
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0b6666a17a9d4588904401163db0c4b7
Source dataset
uspto-grants-2011_10
Patent number
US08044073B2

Reaction notes

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