Hydrochloric Acid → 3-Chloro-5-fluoro-4-(hydroxymethyl)phenol

HRID 1772874Notes

Reaction equation

HRID 1772874 reaction equation
[Cl: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>[Cl: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 27737133-Chloro-5-fluorophenol

Product 1

HCID 222200093-Chloro-5-fluoro-4-(hydroxymethyl)phenolYield 39.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

3-Chloro-5-fluorophenol (703 mg, 4.8 mmol) was added to a solution of potassium hydroxide (297 mg, 5.3 mmol) in H2O (1.45 mL) and heated at 60° C. Formaldehyde (37 wt % in H2O, 0.74 mL, 9.12 mmol) in H2O (1.45 mL) was added dropwise and the reaction mixture left to stir at 40° C. overnight. The reaction mixture was cooled to rt and conc. HCl (approximately 6 mL) was added. The resultant precipitate was filtered, washed with H2O and dried to yield the title compound as a cream solid (334 mg, 1.89 mmol).

Workup

  1. waitthe reaction mixture left
  2. temperatureThe reaction mixture was cooled to rt
  3. filtrationThe resultant precipitate was filtered
  4. washwashed with H2O
  5. customdried

Sources & evidence

ORD record
ord-62ff4e8eb3c94d62b31885e78badbe38
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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