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

HRID 1862639Notes

Reaction equation

HRID 1862639 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]O)=[CH:4][C:3]=1[O:10][CH3:11].[C-:12]#[N:13].[Na+].[C:15]1([C:21]#[C:22][CH2:23]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[CH3:11][O:10][C:3]1[CH:4]=[C:5]([CH2:6][C:12]#[N:13])[CH:8]=[CH:9][C:2]=1[O:1][CH2:23][C:22]#[C:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 62348Vanillyl alcoholHCID 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-benzyl alcohol (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-6b223b8e55204ba3a9700d99344b1ac3
Source dataset
uspto-grants-2003_03
Patent number
US06538159B2

Reaction notes

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