Lawesson's reagent → 7-hydroxy-3-methylisobenzofuran-1(3H)-thione

HRID 1729168Notes

Reaction equation

HRID 1729168 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:9](=O)[O:8][CH:7]2[CH3:12].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:22])=CC=1>C1(C)C(C)=CC=CC=1>[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:9](=[S:22])[O:8][CH:7]2[CH3:12]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 4877821(3H)-Isobenzofuranone, 7-hydroxy-3-methyl-

Product 1

HCID 1355484557-hydroxy-3-methylisobenzofuran-1(3H)-thione

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3.9 g of 7-hydroxy-3-methyl-phthalide (see Examples 101 and 111) and 5.1 g of Lawesson reagent are heated in 20 ml of xylene for 4 hours at 140° C. Chromatographic filtration of the mixture on silica gel [eluant: ethyl acetate/n-hexane (1:9)] yields 7-hydroxy-3-methyl-isobenzofuran-1(3H)-thione, m.p. 39°-41° C.; IR spectrum (CHCl3): C=O 1624, 1604, 1368, 1330, 1304, 1165 cm-1 ; mass spectrum: 180 (M+ =100), 165(58), 137(24).

Workup

  1. filtrationChromatographic filtration of the mixture on silica gel [eluant: ethyl acetate/n-hexane (1:9)]

Sources & evidence

ORD record
ord-8ffaa432636a4f019ca5660648db3a18
Source dataset
uspto-grants-1994_07
Patent number
US05332717

Reaction notes

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