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

HRID 2079164Notes

Reaction equation

HRID 2079164 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 organic layer 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 organic layer 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-2828f5c44cea44e993da06a405ad6563
Source dataset
uspto-grants-2011_04
Patent number
US07928228B2

Reaction notes

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