Sodium Iodide → 1-{[(Methylsulfanyl)methoxy]methyl}naphthalene

HRID 1719233Notes

Reaction equation

HRID 1719233 reaction equation
[CH3:1][S:2][CH2:3]Cl.[Na].[C:6]1([CH2:16][OH:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.[I-].[Na+]>COCCOC>[C:6]1([CH2:16][O:17][CH2:3][S:2][CH3:1])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 16916Chloromethyl methyl sulfideHCID 209081-NaphthalenemethanolHCID 5360545Sodium

Product 1

HCID 156504751-{[(Methylsulfanyl)methoxy]methyl}naphthaleneYield 50%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Methylthiomethyl 1-naphthylmethyl ether was prepared by the reaction of chloromethyl methyl sulfide with the sodium salt of naphthalene-1-methanol in DME in the presence of sodium iodide as described for analogous reactions by E. J. Corey and M. C. Bock in Tetrahedron letters 38 3269(1975); yield 50%, b.p. 105°-115° C./0.01 mmHg. 1H NMR (CDCl3): δ2.17 (Me), 4.70 (CH2S), 5.01 (CH2Naph), 7.1-8.2 (Naph).

Sources & evidence

ORD record
ord-5b56c149de16436c93e31c66a72c174d
Source dataset
uspto-grants-1985_09
Patent number
US04539324

Reaction notes

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