Chloromethyl Methyl Ether → HCID 9990880, compound

HRID 654699Notes

Reaction equation

HRID 654699 reaction equation
O[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([OH:12])=[CH:9][CH:8]=[CH:7]2.[C:13](=[O:16])([O-])[O-].[K+].[K+].[CH3:19][O:20][CH2:21]Cl>CC(C)=O>[CH3:19][O:20][CH2:21][O:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2]([CH:13]=[O:16])=[CH:3][CH:4]=[CH:5]2

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 684381,8-Dihydroxynaphthalene

Product 1

HCID 9990880HCID 9990880, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

9.5 g of 8-hydroxy-1-naphthol was dissolved in 210 ml of acetone, to which 22.7 g of hydrous potassium carbonate and 5.43 ml of chloromethyl methyl ether were added and refluxed for one hour under heating. The reaction solution was filtered and the filtrate was concentrated. 12.2 g of thus obtained yellow oily product was dissolved with no further purification into 250 ml of dichloromethane, to which 4.3 g of pyridinium trifluoro acetate and 18.3 g of pyridinium dichromate were added and stirred at a room temperature for 12 hours. After filtering off insoluble matters, the filtrate was concentrated and then purified on silica gel column chromatography (10% ethyl acetatemexane), to obtain in 5.1 g of the above-captioned compound as colorness crystals.

Workup

  1. additionwere added
  2. temperaturerefluxed for one hour
  3. temperatureunder heating
  4. filtrationThe reaction solution was filtered
  5. concentrationthe filtrate was concentrated
  6. dissolution12.2 g of thus obtained yellow oily product was dissolved with no further purification into 250 ml of dichloromethane, to which 4.3 g of pyridinium trifluoro acetate and 18.3 g of pyridinium dichromate
  7. additionwere added
  8. filtrationAfter filtering off insoluble matters
  9. concentrationthe filtrate was concentrated
  10. custompurified on silica gel column chromatography (10% ethyl acetatemexane)

Sources & evidence

ORD record
ord-4ca8de6ce03548768e3f1ae17535953d
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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