Hydrochloric Acid → 4-Dimethylaminobenzyl alcohol

HRID 1757508

Reaction equation

HRID 1757508 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 (830mg, 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-1e00f12ae83842a6ba338e94c3133aa7
Source dataset
uspto-grants-1995_08
Patent number
US05446068

Linked notes

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