Hydrochloric Acid → 3,5-Difluoro-4-(hydroxymethyl)phenol

HRID 750523Notes

Reaction equation

HRID 750523 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.[OH-:10].[K+].[CH2:12]=O.Cl>O>[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[C:7]=1[CH2:12][OH:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 759283,5-Difluorophenol

Product 1

HCID 222199753,5-Difluoro-4-(hydroxymethyl)phenolYield 49.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 3,5-difluorophenol (25 g, 0.19 mol) and KOH (85%, 12.7 g, 0.19 mol) was treated dropwise with water (50 mL), stirred at 60° C. for 1 h, treated dropwise with formaldehyde solution (37%, 15.6 mL, 0.19 mol) and water (50 mL) and stirred overnight at 40° C. The mixture was cooled, acidified with 6-M HCl, filtered and the resulting solid washed with water and dried to give the title compound (15 g, 49%) as a white solid: NMR δH (400 MHz, DMSO) 10.28 (1H, s), 6.43 (2H, m), 4.99 (1H, t, J 5.6 Hz) and 4.37 (2H, d, J 5.6 Hz).

Workup

  1. stirringstirred overnight at 40° C
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe resulting solid washed with water
  5. customdried

Sources & evidence

ORD record
ord-29b44de4d8124cda92bd91a2724f2455
Source dataset
uspto-grants-2008_07
Patent number
US07405219B2

Reaction notes

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