Diketene → HCID 20360652, compound

HRID 2082788Notes

Reaction equation

HRID 2082788 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[CH3:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[CH:10]=1>F>[C:4]([C:10]1[C:11]2[C:16](=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[O:8][CH3:7])(=[O:5])[CH2:3][C:2]([CH3:1])=[O:6]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 796272,6-Dimethoxynaphthalene

Product 1

HCID 20360652HCID 20360652, compound

Reagents, catalysts & solvents 1

HCID 14917Hydrofluoric AcidSolvent

Procedure

33.6 g (0.4 mol) of diketene were added drop by drop, while stirring at -30° C, to 37.6 g (0.2 mol) of 2,6-dimethoxynaphthalene in 200 ml of anhydrous hydrofluoric acid and the mixture was stirred for another 8 hours at said temperature. The hydrogen fluoride was distilled off under reduced pressure at a temperature of the still of -30° C and the residue washed until it was free from acid. After sublimation of unreacted starting product (11 g = 71 % conversion) colorless crystals of 1-acetoacetyl-2,6-dimethoxynaphthalene melting at 88° C were obtained by column chromatography (silica gel, 0.065 - 0.2 mm, CH2Cl2) in an amount of 35 g (90 % calculated on 2,6-dimethoxynaphthalene).

Workup

  1. distillationThe hydrogen fluoride was distilled off under reduced pressure at a temperature of the still of -30° C
  2. washthe residue washed until it

Sources & evidence

ORD record
ord-aa689b3920f84e9c823d7857ca618380
Source dataset
uspto-grants-1978_04
Patent number
US04082807

Reaction notes

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