Water → 3-[(dimethylamino)methyl]Benzenemethanol

HRID 1493176Notes

Reaction equation

HRID 1493176 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8](OC)=[O:9])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:15][N:2]([CH2:3][C:5]1[CH:6]=[C:7]([CH2:8][OH:9])[CH:12]=[CH:13][CH:14]=1)[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 12810605Methyl 3-(dimethylcarbamoyl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 129520183-[(dimethylamino)methyl]BenzenemethanolYield 55.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(N,N-Dimethylamino carbonyl)benzoic acid, methyl ester (36 g) in dry tetrahydrofuran was added to lithium aluminium hydride (16.6 g) in dry tetrahydrofuran. The reaction mixture was heated at 60° for 3 hours, cooled and treated with water. The solvent was removed and the residue treated with dilute hydrochloric acid. The mixture was basified with sodium hydroxide and extracted with chloroform. The organic extracts were dried and distilled to give an oil (16 g) b.p. 95°-100° (0.1 mm). TLC silica/methanol Rf 0.57.

Workup

  1. temperatureThe reaction mixture was heated at 60° for 3 hours
  2. temperaturecooled
  3. customThe solvent was removed
  4. additionthe residue treated with dilute hydrochloric acid
  5. extractionextracted with chloroform
  6. customThe organic extracts were dried
  7. distillationdistilled

Sources & evidence

ORD record
ord-0c0deb5f8e8e4500a4a15bb5ba04f1e8
Source dataset
uspto-grants-1991_06
Patent number
US05021429

Reaction notes

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