Hydrochloric Acid → 3-Fluoro-2-hydroxymethyl-6-methoxyphenol

HRID 1161434Notes

Reaction equation

HRID 1161434 reaction equation
[F:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([OH:10])[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1.C1COCC1.[BH4-].[Na+].Cl>C(O)C>[F:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([OH:10])[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 224828186-Fluoro-2-hydroxy-3-methoxybenzaldehyde

Product 1

HCID 670969663-Fluoro-2-hydroxymethyl-6-methoxyphenolYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6.85 g of 6-fluoro-2-hydroxy-3-methoxybenzaldehyde [CAS No. 457628-15-8] in 200 ml of an ethanol:THF=1:1 mixed solvent there was added 1.52 g of sodium borohydride while cooling on ice. After stirring at room temperature for 30 minutes, 1N hydrochloric acid was added to the reaction mixture while cooling on ice. The reaction mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off, and the filtrate was concentrated under reduced pressure to give 3-fluoro-2-hydroxymethyl-6-methoxyphenol (6.1 g, crude product).

Workup

  1. temperaturewhile cooling on ice
  2. temperaturewhile cooling on ice
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe desiccating agent was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2116b4c353824c648afb59cf4824e392
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

Loading…