Sodium Cyanide → HCID 21472371, compound

HRID 2294978Notes

Reaction equation

HRID 2294978 reaction equation
[C-]#N.[Na+].[Br:4][C:5]1[CH:19]=[CH:18][C:8]([C:9]([O:11][C:12]2C=CC=[CH:14][CH:13]=2)=[O:10])=[C:7]([OH:20])[CH:6]=1>C(O)CC>[Br:4][C:5]1[CH:19]=[CH:18][C:8]([C:9]([O:11][CH2:12][CH2:13][CH3:14])=[O:10])=[C:7]([OH:20])[CH:6]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 21472384HCID 21472384, compound

Product 1

HCID 21472371HCID 21472371, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

Sodium cyanide was added to a solution of phenyl 4-bromo-2-hydroxybenzoate (1.45 g) in 1-propanol (10 ml). The mixture was heated at reflux for 18 hours. The reaction mixture was cooled to ambient temperature and evaporated. The residue was partitioned between ether and water. The ether phase was separated, dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica gel (Varian Bond Elut S1 silica) using 10% ethyl acetate in pentene as eluent to give n-propyl 4-bromo-2-hydroxybenzoate (1 g), NMR: 1.0(3H,t), 1.72(2H,m), 4.28(2H,t), 7.15(1H,m), 7.24(1H,m), 7.7(1H,d) and 10.7(1H,s).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 hours
  3. customevaporated
  4. customThe residue was partitioned between ether and water
  5. customThe ether phase was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel (Varian Bond Elut S1 silica)

Sources & evidence

ORD record
ord-810e64a7aab74dc3a12dcca3e1caf571
Source dataset
uspto-grants-1997_11
Patent number
US05691349

Reaction notes

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