Sodium Cyanide → HCID 18973736, compound

HRID 2395028Notes

Reaction equation

HRID 2395028 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15]C)[CH:12]=[CH:11][C:10]=1[CH2:17][CH2:18][CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[Na+]>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:27][CH:28]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 18973873HCID 18973873, compound

Product 1

HCID 18973736HCID 18973736, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
190 °C

Procedure

To a solution of 4-[3-(2-benzyloxy-4-methoxyphenyl)-propyl]benzoic acid (0.75 g) in DMSO (20 ml) was added sodium cyanide (0.5 g). The reaction mixture was heated at 190° C. for 40 hours, cooled, partitioned between 1N aqueous NaOH and diethyl ether. The aqueous layer was separated, acidified to pH1 (conc. HCl) and extracted with ethyl acetate. The organic solution was dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica gel eluting with diethyl ether, and crystallisation from CH2Cl2 /hexane mixtures to give the title compound (150 mg).

Workup

  1. temperaturecooled
  2. custompartitioned between 1N aqueous NaOH and diethyl ether
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic solution was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel eluting with diethyl ether, and crystallisation from CH2Cl2 /hexane

Sources & evidence

ORD record
ord-25c1ce94223546d6a40bd977a5e668ed
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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