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

HRID 1169557Notes

Reaction equation

HRID 1169557 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].OS(O)(=O)=O.[C:12]([C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)#[N:13]>CCOCC>[NH2:13][CH2:12][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][OH:19])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 120874-Cyanobenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 6496943[4-(Aminomethyl)phenyl]methanolYield 70.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Adapting the procedure described by Keppler et al., Nature Biotechnology 21, 86-89 (2003), 1.5 L of 0.5 M LiAlH4 were chilled on ice and 22 mL of concentrated H2SO4 were added dropwise. 4-Cyanobenzoic acid (10) 20 g (136 mmol) was suspended in 120 mL of ether and this was added dropwise to the sulfuric acid. The reaction was heated to reflux for 4 hours. The reaction was quenched on ice with 215 mL of water followed by the addition of 80 g of NaOH in 650 mL of water. The ether was decanted off the resulting gel and the gel was extracted twice with 600 mL portions of ether. The combined ether fractions were dried over MgSO4 and evaporated under vacuum to give 13.1 g (96 mmol) of 4-(aminomethyl)benzyl alcohol (11) as a clear oil. 1H NMR (CDCL3/TMS) δ=1.95 (broad s, 3H, —OH and —NH2, exchangeable with D2O), 3.86 (s, 2H, —CH2—NH2), 4.68 (s, 2H, —CH2—OH), 7.30 (m, 4H, aromatic).

Workup

  1. additionwere added dropwise
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 4 hours
  4. customThe reaction was quenched on ice with 215 mL of water
  5. additionfollowed by the addition of 80 g of NaOH in 650 mL of water
  6. customThe ether was decanted off the resulting gel
  7. extractionthe gel was extracted twice with 600 mL portions of ether
  8. dry with materialThe combined ether fractions were dried over MgSO4
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-64464a6d547d4824ade147ac1fd700a9
Source dataset
uspto-grants-2010_11
Patent number
US07825096B2

Reaction notes

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