1,4-dihydro-3H-2-benzopyran-3-one → (2-Hydroxymethylphenyl)acetonitrile

HRID 842328Notes

Reaction equation

HRID 842328 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3](=O)[O:2]1.ClCC1C(CC#[N:22])=CC=CC=1>>[OH:2][CH2:1][C:10]1[C:5]([CH2:4][C:3]#[N:22])=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 780921,4-dihydro-3H-2-benzopyran-3-one2×HCID 112981592-(Cyanomethyl)benzyl chloride

Product 1

HCID 582335(2-Hydroxymethylphenyl)acetonitrileYield 1.6%

Procedure

After completion of the reaction, the concentration of 3-isochromanone was analyzed by GC analysis and then the yield of 3-isochromanone was calculated. As a result, the yield was found to be 95% based on α-chloro-α′-cyano-o-xylene. At this time, the conversion ratio of α-chloro-α′-cyano-o-xylene was 100% and the by-product compound (α-hydroxy-α′-cyano-o-xylene) where the halogen moiety was hydrolyzed was produced in a yield of 1.6%.

Workup

  1. customAfter completion of the reaction

Sources & evidence

ORD record
ord-c863c88ef68940f4a2f54393860c9c46
Source dataset
uspto-grants-2002_04
Patent number
US06372921B1

Reaction notes

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