Water → [3-Methoxy-4-(3-phenyl-prop-2-ynyloxy)-phenyl]-acetonitrile

HRID 1862500Notes

Reaction equation

HRID 1862500 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[O:11][CH3:12].[C-]#N.[Na+].[C:16]1([C:22]#[C:23][CH2:24]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C)C=O>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([CH2:8][C:9]#[N:10])[CH:6]=[CH:7][C:2]=1[O:1][CH2:24][C:23]#[C:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 782204-Hydroxy-3-methoxyphenylacetonitrileHCID 105173333-Phenylprop-2-yn-1-yl 4-methylbenzene-1-sulfonate

Product 1

HCID 18619867[3-Methoxy-4-(3-phenyl-prop-2-ynyloxy)-phenyl]-acetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of (4-hydroxy-3-methoxy-phenyl)-acetonitrile (17.4 g) and sodium cyanide (6.6 g) in dimethylformamide (250 ml) is stirred under an atmosphere of nitrogen for 3 hours at +120° C. The mixture is then cooled to +60° C. and toluene-4-sulfonic acid 3-phenyl-prop-2-ynyl ester (39 g) in dimethylformamid (50 ml)is added during 5 minutes. It is stirred at +65° C. for another 4 hours. Upon cooling water (800 ml) is added. The mixture is extracted with ethyl acetate (2×500 ml). The organic phases are washed with brine (2×500 ml), dried (MgSO4) and evaporated. The residue is purified by flash column chromatography on silica gel (ethyl acetate/hexane 1:3) and recrystallised from ethyl acetate/hexane. [3-Methoxy-4-(3-phenyl-prop-2-ynyloxy)-phenyl]-acetonitrile is obtained, m.p. 74-75° C.

Workup

  1. temperatureThe mixture is then cooled to +60° C.
  2. stirringIt is stirred at +65° C. for another 4 hours
  3. additionis added
  4. extractionThe mixture is extracted with ethyl acetate (2×500 ml)
  5. washThe organic phases are washed with brine (2×500 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue is purified by flash column chromatography on silica gel (ethyl acetate/hexane 1:3)
  9. customrecrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-7b7e705f691246bf9880ccde96e9e202
Source dataset
uspto-grants-2003_03
Patent number
US06538016B2

Reaction notes

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