Chloromethyl Methyl Ether → HCID 14986453, compound

HRID 654679Notes

Reaction equation

HRID 654679 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:12])[C:5]([CH:13]=[O:14])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:24][O:25][CH2:26]Cl>ClCCl>[CH3:24][O:25][CH2:26][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:12])[C:5]([CH:13]=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 149864524-Hydroxy-5-methyl-1-naphthalenecarbaldehyde

Product 1

HCID 14986453HCID 14986453, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

18 g of 4-hydroxy-5-methyl-1-naphthalenecarbaldehyde and 15 g of N,N-diisopropylethylamine were dissolved in 200 ml of dichloromethane, in which 9.3 g of chloromethyl methyl ether was gradually dropped under ice-cooling conditions. After agitation at room temperature overnight, the reaction solution was washed with water and dried with anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by silica gel column chromatography (10% ethyl acetate/hexane) to obtain 16.8 g of the captioned compound as light brown crystals.

Workup

  1. additionwas gradually dropped under ice-
  2. temperaturecooling conditions
  3. washAfter agitation at room temperature overnight, the reaction solution was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ee8ba4db2e5a4e95aed757e990c17f10
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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