Hydrochloric Acid → 4-Bromo-2-(hydroxymethyl)-6-methoxyphenol

HRID 1157935Notes

Reaction equation

HRID 1157935 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(O)C.[BH4-].[Na+].Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([OH:10])=[C:6]([CH2:7][OH:8])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 2622385-Bromo-2-hydroxy-3-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 8940924-Bromo-2-(hydroxymethyl)-6-methoxyphenolYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 200 ml solution of 50 g of 5-bromo-2-hydroxy-3-methoxybenzaldehyde in an ethanol:THF=1:1 mixed solvent there was added 16.4 g of sodium borohydride while cooling on ice. After stirring for 2 hours at room temperature, 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 desiccant was filtered out and the filtrate was concentrated under reduced pressure to obtain the target compound (50 g) as a 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 desiccant was filtered out
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-06294e2154934eb6b935b5e72e55bad4
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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