3-Hydroxybenzaldehyde → 3-Hydroxybenzyl alcohol

HRID 1808726Notes

Reaction equation

HRID 1808726 reaction equation
[BH4-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8].O.Cl>CCO.ClCCl>[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][OH:8]

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydride

Product 1

HCID 1023-Hydroxybenzyl alcohol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

NaBH4 (775 mg, 20.5 mmol) is gradually added to a solution of 3-hydroxybenzaldehyde (5 g, 40.9 mmol) in EtOH (25 mL) while cooling the reaction mixture with cold water. This mixture is stirred for 5-10 min at the same temperature. And then dichloromethane (DCM) (100 mL) is added followed by a 2M HCl aqueous solution (until pH ˜3). The organic phase is separated and the final product is extracted 4 times from the aqueous phase with a EtOH/DCM mixture in the proportion of 1:3. The collected organic phases are dried on Na2SO4. After evaporation of the solvents under reduced pressure, a viscous colorless oil is obtained (4.9 g, 97%), which gradually crystallizes.

Workup

  1. customThe organic phase is separated
  2. extractionthe final product is extracted 4 times from the aqueous phase with a EtOH/DCM mixture in the proportion of 1:3
  3. customThe collected organic phases are dried on Na2SO4
  4. customAfter evaporation of the solvents under reduced pressure
  5. customa viscous colorless oil is obtained (4.9 g, 97%), which
  6. customgradually crystallizes

Sources & evidence

ORD record
ord-040cf873c16a4e548bb16d90d3ef58c4
Source dataset
uspto-grants-2013_01
Patent number
US08361993B2

Reaction notes

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