Methyl iodide → HCID 13251053, compound

HRID 845545Notes

Reaction equation

HRID 845545 reaction equation
[C:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[CH:7][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2].CI.[CH2:20]1CCN2C(=NCCC2)CC1>O1CCCC1>[C:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15][CH3:20])=[CH:7][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 313125HCID 313125, compound

Product 1

HCID 13251053HCID 13251053, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-acetyloxy-2-methoxy-4-hydroxynaphthalene (23.2 g) and methyl iodide (6.4 mL) in tetrahydrofuran (250 mL) was treated dropwise with a solution of DBU (16.5 mL) in tetrahydrofuran (50 mL). The resulting precipitate of DBU.HI was removed by filtration, and the filtrate evaporated. Recrystallization from methanol gave 1-acetyloxy-2,4-dimethoxynaphthalene, m.p. 116°-117° C.

Workup

  1. customHI was removed by filtration
  2. customthe filtrate evaporated
  3. customRecrystallization from methanol

Sources & evidence

ORD record
ord-e6ec10503b4049b1911b93ad0225b257
Source dataset
uspto-grants-1988_07
Patent number
US04758587

Reaction notes

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