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

HRID 1729170Notes

Reaction equation

HRID 1729170 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(=S)SP(C3C=CC(OC)=CC=3)(=S)[S:22]2)=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

1.67 g of 7-hydroxy-3-methyl-phthalide (see Example 101) and 2.17 g of 2,4-bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetan (Lawesson reagent) are heated in 8 ml of xylene at 138° C. for 3 hours. When it has cooled, the reaction material is filtered directly over a column of silica gel [eluant: ethyl acetate/n-hexane (1:4)] in order to isolate the 7-hydroxy-3-methyl-isobenzofuran-1(3H)-thione; m.p. 38°-40° C.; IR spectrum: 1624, 1604, 1368, 1330, 1304, 1165 cm-1 ; mass spectrum: 180 (M+ =100), 165 (58), 137 (24).

Workup

  1. temperatureWhen it has cooled
  2. filtrationthe reaction material is filtered directly over a column of silica gel [eluant: ethyl acetate/n-hexane (1:4)] in order

Sources & evidence

ORD record
ord-986fac88168e435691bc5065bfaa6182
Source dataset
uspto-grants-1994_07
Patent number
US05332717

Reaction notes

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