Formaldehyde → (4-Fluoro-2-methylphenyl)methanol

HRID 1164351Notes

Reaction equation

HRID 1164351 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9].[Mg].[O:11]1CCC[CH2:12]1.C=O>C(O)(=O)C>[F:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:12][OH:11])=[C:3]([CH3:9])[CH:4]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 967432-Bromo-5-fluorotolueneHCID 5462224Magnesium

Product 1

HCID 3872017(4-Fluoro-2-methylphenyl)methanolYield 47.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred and refluxing Grignard-complex, previously prepared starting from 39.7 parts of 1-bromo-4-fluoro-2-methylbenzene and 5.1 parts of magnesium in 225 parts of tetrahydrofuran, are added portionwise 8.4 parts of paraformaldehyde. Upon completion, stirring is continued for 1 hour at reflux. The reaction mixture is cooled and poured onto a mixture of crushed ice and acetic acid. The product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is distilled, yielding 14 parts (47.6%) of 4-fluoro-2-methylbenzenemethanol; bp. 110° C. (water-jet).

Workup

  1. temperaturerefluxing Grignard-complex
  2. custompreviously prepared
  3. stirringUpon completion, stirring
  4. temperatureat reflux
  5. temperatureThe reaction mixture is cooled
  6. extractionThe product is extracted with trichloromethane
  7. customThe extract is dried
  8. filtrationfiltered
  9. customevaporated
  10. distillationThe residue is distilled

Sources & evidence

ORD record
ord-e8d4298c7d1240259a3a5c3b87a9d5d5
Source dataset
uspto-grants-1983_01
Patent number
US04369184

Reaction notes

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