Methanesulfenylchloride → 1-[(Chloromethoxy)methyl]naphthalene

HRID 1719234Notes

Reaction equation

HRID 1719234 reaction equation
S(Cl)(Cl)(=O)=O.C1C2C(=CC=CC=2)C=CC=1.[C:16]1([CH2:26][O:27][CH2:28]SC)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.CS[Cl:33]>ClCCl>[Cl:33][CH2:28][O:27][CH2:26][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 138595MethanesulfenylchlorideHCID 156504751-{[(Methylsulfanyl)methoxy]methyl}naphthaleneHCID 22556242HCID 22556242, compound

Product 1

HCID 134082881-[(Chloromethoxy)methyl]naphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Chloromethyloxymethyl)naphthalene Sulfuryl chloride (12 mmol) in dry dichloromethane (20 mmol) was added dropwise with stirring to a solution of methylthiomethyl 1-naphthylmethyl ether (12 mmol) in dry dichloromethane (40 ml) at room temperature. After stirring for 30 min the solvent and methanesulfenyl chloride formed in the reaction were distilled off at reduced pressure. The residual material was used for alkylation without further purification. 1H NMR (CDCl3): δ5.13 (CH2), 5.47 (CH2Cl), 7.2-8.3 (Naph).

Workup

  1. customformed in the reaction
  2. distillationwere distilled off at reduced pressure
  3. customThe residual material was used for alkylation without further purification

Sources & evidence

ORD record
ord-a69b9863163d4784871dc425371f3af4
Source dataset
uspto-grants-1985_09
Patent number
US04539324

Reaction notes

Loading…