Hydrochloric Acid → 4-Dimethylaminobenzyl alcohol

HRID 6496

Reaction equation

HRID 6496 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[BH4-].[Na+].Cl>C(O)C>[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 74794-(Dimethylamino)BenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 1371664-Dimethylaminobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Mix 4-dimethylaminobenzaldehyde (3.3 g, 22 mmol), sodium borohydride (830 mg, 22 mmol) and absolute ethanol (25 mL). Stir at room temperature until the reaction is complete, pour onto dilute hydrochloric acid and extract into ethyl acetate. Separate the organic phase and extract the aqueous phase with ethyl acetate (2×). Combine the organic phases and dry (MgSO4). Evaporate the solvent in vacuo and purify by silica gel chromatography to give 4-(dimethylamino)benzyl alcohol.

Workup

  1. extractionextract into ethyl acetate
  2. customSeparate the organic phase
  3. extractionextract the aqueous phase with ethyl acetate (2×)
  4. dry with materialCombine the organic phases and dry (MgSO4)
  5. customEvaporate the solvent in vacuo
  6. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-d66256aab42c4645ba01c94ac4791f03
Source dataset
uspto-grants-1993_09
Patent number
US05248825

Linked notes

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