Methyl chloroformate → 1-Methoxycarbonyloxy-2,4-dimethoxynaphthalene

HRID 845550Notes

Reaction equation

HRID 845550 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[O:14][CH3:15].Cl[C:17]([O:19][CH3:20])=[O:18].C(N(CC)CC)C>O1CCCC1>[CH3:20][O:19][C:17]([O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[O:14][CH3:15])=[O:18]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 125635471-Hydroxy-2,4-dimethoxynaphthalene

Product 1

HCID 141830431-Methoxycarbonyloxy-2,4-dimethoxynaphthalene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.27 g of 1-hydroxy-2,4-dimethoxynaphthalene, prepared as shown in Preparations 7 and 8, in 50 ml of tetrahydrofuran was added 0.694 g of methyl chloroformate followed by 0.743 g of triethylamine. The mixture was stirred at room temperature for 16 hours, filtered, then the solvent removed under reduced pressure. The residue was dissolved in diethyl ether, washed with dilute hydrochloric acid and dried over anhydrous sodium sulfate. The ether was removed under reduced pressure and the residue chromatographed on silica gel, eluting with a 1:1 mixture of methylene chloride and hexane, to give 1-methoxycarbonyloxy-2,4-dimethoxynaphthalene, m.p. 128°-129° C.

Workup

  1. filtrationfiltered
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe residue was dissolved in diethyl ether
  4. washwashed with dilute hydrochloric acid
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe ether was removed under reduced pressure
  7. customthe residue chromatographed on silica gel
  8. washeluting with a 1:1 mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-491d38055b8941879eaac8e71da4597d
Source dataset
uspto-grants-1988_07
Patent number
US04758587

Reaction notes

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