Diethyl Ether → 9-Acetoxyxanthene

HRID 1605148Notes

Reaction equation

HRID 1605148 reaction equation
CN[C:3]([O:5][CH:6]1[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:13][C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:4].[CH3:20]COCC>C(O)(=O)C>[C:3]([O:5][CH:6]1[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:13][C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)(=[O:4])[CH3:20]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 21482819HCID 21482819, compound

Product 1

HCID 125434549-Acetoxyxanthene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 15 g. of 9-(N-methylcarbamoyloxy)xanthene, suspended in 200 ml. of dry ether, was added 18 ml. of glacial acetic acid with stirring. After one hour, the lower acid layer was removed. The ether phase was then cooled, neutralized with cold aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was recrystallized from benzene-hexane to give 9-acetoxyxanthene, m.p. 109°-112° C.

Workup

  1. customthe lower acid layer was removed
  2. temperatureThe ether phase was then cooled
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from benzene-hexane

Sources & evidence

ORD record
ord-2d5ab999f8a64ae5a8cd35d518a6d89a
Source dataset
uspto-grants-1976_04
Patent number
US03949076

Reaction notes

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