4-Methoxyphenyl-1,3-dithiolane → 1-Methoxy-4-(trichloromethyl)benzene

HRID 482785Notes

Reaction equation

HRID 482785 reaction equation
[CH3:1][O:2]C1C=CC(C2SCCS2)=CC=1.COC1C=C(C=CC=1)C(Cl)Cl.CO[C:27]1[CH:28]=[C:29]([C:33]([Cl:36])([Cl:35])[Cl:34])[CH:30]=[CH:31][CH:32]=1>>[CH3:1][O:2][C:32]1[CH:27]=[CH:28][C:29]([C:33]([Cl:34])([Cl:35])[Cl:36])=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 231754-Methoxyphenyl-1,3-dithiolaneHCID 13070690HCID 13070690, compoundHCID 20245107HCID 20245107, compound

Product 1

HCID 125706841-Methoxy-4-(trichloromethyl)benzene

Procedure

5.8 gm (0.0274 moles) of the dithiolane of Example 4 was reacted following the procedure of Example 6 to give 5.01 gm of a 3.8:1 mixture of 3-methoxybenzaldichloride and 3-methoxybenzotrichloride (b.p. 83°-84° C. at 0.3 mm/Hg). NMR and GC/MS Analysis for Product: 1H--NMR (CDCl3), δ3.63 (S, 3H, OCH3), 6.7 (d, J=13.5 Hz, 2H), 7.65 (d, J=13.5 Hz, 2H); GCMS (70 ev), M/e (% rel. int.) 228 (M+ +4, 3.3), 226 (M+ +2, 9.2), 224 (M+, 9), 193 (17), 191 (93), 189 (100).

Workup

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Sources & evidence

ORD record
ord-a146a18857a049458d01fbc273f2564d
Source dataset
uspto-grants-1986_03
Patent number
US04575565

Reaction notes

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