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

HRID 842329Notes

Reaction equation

HRID 842329 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 2.2%

Procedure

After the completion of 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 75% 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 α-hydroxy-α′-cyano-o-xylene was produced in a yield of 2.2%. Furthermore, as a result of the HPLC analysis, α-carboxy-α′-hydroxy-o-xylene and α-aminocarboxy-α′-hydroxy-o-xylene were found to be present as by-products in a concentration of 18% based on α-chloro-α′-cyano-o-xylene.

Workup

  1. customAfter the completion of reaction

Sources & evidence

ORD record
ord-3129a3fee5bb49c59ec9272e16c5e7df
Source dataset
uspto-grants-2002_04
Patent number
US06372921B1

Reaction notes

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