Water → (4-(4-Aminobutyl)phenyl)methanol

HRID 81309Notes

Reaction equation

HRID 81309 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]=[N+]=[N-])=[CH:13][CH:12]=1)(O)=O.[OH2:24].[OH-].[Na+]>C1COCC1>[OH:24][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22566167[4-(4-Azidobutyl)phenyl]acetic acid

Product 1

HCID 11550093(4-(4-Aminobutyl)phenyl)methanolYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (35 mL of a 1.0 M solution in THF, 0.035 mol) was added drop wise to a vigorously stirred solution of 4-(4-carboxymethylphenyl)butylazide 8 (2.4 g, 0.010 mol) in dry THF (120 mL) at 0° C. and stirred overnight at room temperature under a nitrogen atmosphere. To break up the complex water (1.5 mL), 15% NaOH (1.5 mL) and water (4.5 mL) were added drop wise to the cold reaction mixture. The white solid precipitate was filtered off and washed with THF. All organics phases were combined and evaporated. The material was purified by column chromatography (silica gel, 2:1:0.05 chloroform/ethanol/concentrated ammonium hydroxide) to provide 67 (1.17 g, 64%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.15 (br s, 2H), 1.54 (br s, 2H) 1.70 (br s, 2H), 2.60 (m, 4H), 3.77 (s, 1H), 4.67 (s, 2H), 7.47 (s, 2H), 7.60 (s, 2H).

Workup

  1. additionwere added drop
  2. customwise to the cold reaction mixture
  3. filtrationThe white solid precipitate was filtered off
  4. washwashed with THF
  5. customevaporated
  6. customThe material was purified by column chromatography (silica gel, 2:1:0.05 chloroform/ethanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-808da0c99267462faa05496fdb05930e
Source dataset
uspto-grants-2014_09
Patent number
US08846688B2

Reaction notes

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