Hydrochloric Acid → 5-Bromo-2-hydroxybenzyl alcohol

HRID 1081867Notes

Reaction equation

HRID 1081867 reaction equation
[Br:1][C:2]1[CH:10]=[C:6]([C:7](O)=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl.C(OCC)(=O)C>CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH2:7][OH:8])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 69725-Bromosalicylic acidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 753425-Bromo-2-hydroxybenzyl alcoholYield 76.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under ice cooling, the solution of 5-bromosalicylic acid (21.7 g) in ether (200 ml) was slowly added dropwise to the suspension of LiAlH4 (5.7 g) in ether (200 ml). After stirring at room temperature for 30 minutes, the reaction solution was slowly poured into 3N HCl with floating ice for extraction with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The oily residue generated after the evaporation of the solvent under reduced pressure was crystallized from ether-hexane, and the crystal was filtered, to give the title compound (15.5 g; 76.5%).

Workup

  1. washThe organic phase was washed with saturated sodium chloride solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. customafter the evaporation of the solvent under reduced pressure
  4. customwas crystallized from ether-hexane
  5. filtrationthe crystal was filtered

Sources & evidence

ORD record
ord-1219eaa45e474aeea25a74e1827ca1ca
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

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