Diethyl Ether → 9-Acetoxyxanthene

HRID 1973242Notes

Reaction equation

HRID 1973242 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, is added 18 ml. of glacial acetic acid with stirring. After 1 hour, the lower acid layer is removed. The ether phase is then cooled, neutralized with cold aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is recrystallized from benzene-hexane to give 9-acetoxyxanthene, m.p. 109°-112° C.

Workup

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

Sources & evidence

ORD record
ord-f33f7e9c792d4c819a5f6e7f715a8039
Source dataset
uspto-grants-1976_12
Patent number
US03996364

Reaction notes

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