Triethylamine → 2-Chloromethyl-4,8-dimethoxy-naphthalene

HRID 1005178Notes

Reaction equation

HRID 1005178 reaction equation
CS([Cl:5])(=O)=O.[CH3:6][O:7][C:8]1[C:17]2[C:12](=[C:13]([O:18][CH3:19])[CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([CH2:20]O)[CH:9]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:5][CH2:20][C:10]1[CH:9]=[C:8]([O:7][CH3:6])[C:17]2[C:12](=[C:13]([O:18][CH3:19])[CH:14]=[CH:15][CH:16]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22126362HCID 22126362, compound

Product 1

HCID 221269642-Chloromethyl-4,8-dimethoxy-naphthaleneYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.92 g of methanesulphonyl chloride in 20 ml of methylene chloride was added dropwise to a solution, cooled to -10° C., of 7.7 g (35.3 mmol) of (4,8-dimethoxy-naphthalen-2-yl)-methanol and 4.4 g (38.8 mmol) of triethylamine in 50 ml of methylene chloride. The reaction mixture was stirred at room temperature for 18 hours. For the working-up, the mixture was extracted with 50 ml of ice-cold sodium hydrogen carbonate solution and the aqueous phase was separated and back-extracted with 25 ml of methylene chloride. The combined organic phases were dried over sodium sulphate and subsequently evaporated under reduced pressure. For purification, the residue was filtered over a layer of silica gel using methylene chloride as the eluent. There were obtained 7.2 g of 2-chloromethyl-4,8-dimethoxy-naphthalene as a beige solid; MS: 296 (M)+.

Workup

  1. extractionthe mixture was extracted with 50 ml of ice-cold sodium hydrogen carbonate solution
  2. customthe aqueous phase was separated
  3. extractionback-extracted with 25 ml of methylene chloride
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. customsubsequently evaporated under reduced pressure
  6. customFor purification
  7. filtrationthe residue was filtered over a layer of silica gel

Sources & evidence

ORD record
ord-0733f6ec73fa4a64a508edd503eaf5e3
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

Loading…