Water → 6-Methyl-2-methylaminobenzyl alcohol

HRID 1762184Notes

Reaction equation

HRID 1762184 reaction equation
[CH:1]([NH:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:5]=1[CH2:6][OH:7])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:12][C:8]1[C:5]([CH2:6][OH:7])=[C:4]([NH:3][CH3:1])[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 143684522-Formamido-6-methylbenzyl alcoholHCID 21226445Aluminium lithium hydride

Product 1

HCID 540947806-Methyl-2-methylaminobenzyl alcoholYield 49.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-formamido-6-methylbenzyl alcohol (1.9 g) in tetrahydrofuran (26 ml) was added dropwise to a suspension of lithium aluminum hydride (0.873 g) in tetrahydrofuran (17 ml) at room temperature over a period of 10 minutes. After being refluxed for 4.5 hours, the excess reagent was decomposed with a small amount of water and the resulting precipitates were filtered off by suction. The filtrate was evaporated in vacuo and the residue was recrystallized from carbon tetrachloride to give 6-methyl-2-methylaminobenzyl alcohol (0.86 g).

Workup

  1. temperatureAfter being refluxed for 4.5 hours
  2. customthe resulting precipitates
  3. filtrationwere filtered off by suction
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was recrystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-d1b51f6357394f49aaea3d7e4e62f200
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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