4-(Aminomethyl)Benzoic Acid → [4-(Aminomethyl)phenyl]methanol

HRID 6734

Reaction equation

HRID 6734 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 655264-(Aminomethyl)Benzoic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 6496943[4-(Aminomethyl)phenyl]methanolYield 82.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-aminomethyl-benzoic acid (0.20 g) in 20 mL diethyl ether was cooled to 0° C. Lithium aluminum hydride (0.19 g) was added in portions to the stirring carboxylic acid solution. The resulting slurry was stirred for 20 h and then cooled to 0 C. The mixture was carefully quenched by the sequential addition of 0.2 mL of water followed by 0.2 mL of 3 N sodium hydroxide followed by 0.6 mL of more water. The mixture was stirred for 15 min, then filtered to remove the aluminum salts. The filtrate was collected and the volatile material was evaporated to give 150 mg of (4-aminomethyl-phenyl)-methanol.

Workup

  1. temperaturecooled to 0 C
  2. customThe mixture was carefully quenched by the sequential addition of 0.2 mL of water
  3. stirringThe mixture was stirred for 15 min
  4. filtrationfiltered
  5. customto remove the aluminum salts
  6. customThe filtrate was collected
  7. customthe volatile material was evaporated

Sources & evidence

ORD record
ord-05979e650a604461bc29aa3be1d9d2c3
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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