Hydrochloric Acid → 5,7-di-tert-butyl-3-(4-methylthiophenyl)-3H-benzofuran-2-one

HRID 440149

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]2[O:12][C:11](=[O:13])[CH:10](O)[C:9]=2[CH:15]=1)([CH3:4])([CH3:3])[CH3:2].[C:20]1([S:26][CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl.O>[C:1]([C:5]1[CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]2[O:12][C:11](=[O:13])[CH:10]([C:23]3[CH:24]=[CH:25][C:20]([S:26][CH3:27])=[CH:21][CH:22]=3)[C:9]=2[CH:15]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 26.2 g (0.10 mol) of 5,7-di-tert-butyl-3-hydroxy-3H-benzofuran-2-one (compound (201), Table 2, Example 1a) in 25 ml (0.21 mol) of thioanisole is added dropwise to a solution of 14.7 g (0.11 mol) of aluminium chloride in 15 ml (0.13 mol) of thioanisole at 35°-40° C. The reaction mixture is thereafter stirred for 30 minutes at 30° C. and for 2 hours at 80° C., and then after cooling, c. 50 ml of water and then concentrated hydrochloric acid and methylene chloride are added cautiously in sufficient amount to form a homogeneous two-phase mixture. The organic phase is separated, washed with water, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Crystallisation of the residue from ethanol yields 6.7 g (18% ) of 5,7-di-tert-butyl-3-(4-methylthiophenyl)-3H-benzofuran-2-one, m.p. 125°-131° C. (compound (108), Table 1).

Workup

temperatureafter cooling
customto form a homogeneous two-phase mixture
customThe organic phase is separated
washwashed with water
dry with materialdried over sodium sulfate
concentrationconcentrated on a vacuum rotary evaporator
customCrystallisation of the residue from ethanol

Sources & evidence

ORD record: ord-886248421c8b4875a19e9a138b25eee2
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05516920

Linked notes

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