Solketal → HCID 12806952, compound

HRID 2058595Notes

Reaction equation

HRID 2058595 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18]([OH:20])=[O:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:21][CH3:22])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:23])[CH:5]=1.[CH3:24][C:25]1([CH3:32])[O:29][CH:28]([CH2:30]O)[CH2:27][O:26]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18]([O:20][CH2:30][CH:28]2[CH2:27][O:26][C:25]([CH3:32])([CH3:24])[O:29]2)=[O:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:21][CH3:22])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:23])[CH:5]=1

Participants

4

Reactant 3

HCID 7528SolketalHCID 521998p-Toluenesulfonic acid monohydrateHCID 12806939[(5,6-Dichloro-9a-ethyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetic acid

Product 1

HCID 12806952HCID 12806952, compound

Procedure

A mixture of 2 gm. of [(5,6-dichloro-9a-ethyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]-acetic acid, 3 ml. of 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane and 0.5 g. of p-toluenesulfonic acid hydrate are heated on the steam bath for 3 hours. The dark reaction mixture then is chromatographed on 300 g of silica, and eluted with acetic acid-acetone-toluene (5:5:90). Fractions containing a single component (Rf~0.4) are pooled and concentrated to a yellow oil. On standing overnight, a mixture of crystalline solid and yellow oil resulted. The mixture is filtered and the solid recrystallized from tetrahydrofuran-ether-petroleum ether (5:15:25). The yield of pure product is 0.3 g., m.p. 143°-145° C.

Workup

  1. additionA mixture of 2 gm
  2. customThe dark reaction mixture
  3. customthen is chromatographed on 300 g of silica
  4. washeluted with acetic acid-acetone-toluene (5:5:90)
  5. additionFractions containing a single component (Rf~0.4)
  6. concentrationconcentrated to a yellow oil
  7. additiona mixture of crystalline solid and yellow oil
  8. customresulted
  9. filtrationThe mixture is filtered
  10. customthe solid recrystallized from tetrahydrofuran-ether-petroleum ether (5:15:25)

Sources & evidence

ORD record
ord-ac46fb7d659141efa74f6a0e021e506b
Source dataset
uspto-grants-1982_03
Patent number
US04317922

Reaction notes

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