Diethyl Ether → 9-Acetoxyxanthene

HRID 1415543Notes

Reaction equation

HRID 1415543 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 benezene-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 benezene-hexane

Sources & evidence

ORD record
ord-d79a75d57848459f939050f1473c5a60
Source dataset
uspto-grants-1977_01
Patent number
US04005208

Reaction notes

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