HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Iodide → Methyl 4-{[(methylsulfanyl)methoxy]methyl}benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Chloromethyl methyl sulfide | HCID 16916 | — |
| Reactant | Methyl 4-(hydroxymethyl)benzoate | HCID 81325 | — |
| Reactant | Sodium | HCID 5360545 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | Methyl 4-{[(methylsulfanyl)methoxy]methyl}benzoate | HCID 14898241 | 75% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04539324 |
| Source dataset | uspto-grants-1985_09 |
| ORD ID | ord-a9ebfa24182145d1a7ba39c8b5ae0e09 |
| Source note | uspto-grants-1985_09 |