Sodium Iodide → Methyl 4-{[(methylsulfanyl)methoxy]methyl}benzoate

HRID 1719237Notes

Reaction equation

HRID 1719237 reaction equation
[CH3:1][S:2][CH2:3]Cl.[Na].[OH:6][CH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1.[I-].[Na+]>C(COC)OC>[CH3:1][S:2][CH2:3][O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 16916Chloromethyl methyl sulfideHCID 81325Methyl 4-(hydroxymethyl)benzoateHCID 5360545Sodium

Product 1

HCID 14898241Methyl 4-{[(methylsulfanyl)methoxy]methyl}benzoateYield 75%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

4-(Methyloxycarbonyl)benzyl methylthiomethyl ether was prepared by the reaction of chloromethyl methyl sulphide with the sodium salt of methyl 4-hydroxymethylbenzoate (see G. D. Brindell, L. D. Lillwitz, J. P. Wuskell and A. P. Dunlop, Ind. Eng. Chem. Prod. Res. Dev. 15, 83(1976) in dimethoxyethane in the presence of sodium iodide as described for analogous reactions in E. J. Corey and M. C. Bock, Tetrahedron Letters 38 3269 (1975); yield 75%, b.p. 110°-120° C./0.01 mmHg. 1H NMR (CDCl3): δ2.17 (SMe) 3.92 (OMe), 4.67 (CH2), 4.70 (CH2), 7.2-8.2 (Ph).

Sources & evidence

ORD record
ord-a9ebfa24182145d1a7ba39c8b5ae0e09
Source dataset
uspto-grants-1985_09
Patent number
US04539324

Reaction notes

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