m-Chloroperbenzoic acid → 1-Hydroxytridecan-2-one

HRID 373174Notes

Reaction equation

HRID 373174 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].C[Si](C)(C)[O:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH2:16]>CCCCCC>[OH:6][CH2:14][C:15](=[O:16])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 198120312-Trimethylsilyloxy-1-tridecene

Product 1

HCID 134236451-Hydroxytridecan-2-oneYield 29%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
25 °C

Procedure

3-Chloroperoxybenzoic acid is added in one portion to a cooled (0° C.) solution of 2-trimethylsilyloxy-1-tridecene in hexane (200 mL). The ice bath is removed and the resulting slurry is stirred (4 hours, 25° C.). Ether (200 mL) and 1.5 N HCl (130 mL) are added and the resulting two-phase mixture is stirred vigorously (4.5 hours, 25° C.). The layers are separated and the organic layer is washed with saturated sodium bicarbonate (2×130 mL), washed with brine (1×130 mL), dried (MgSO4), and concentrated in vacuo. The residue is chromatographed on silica (90:10 hexane:ethyl acetate), and concentrated in vacuo. The resulting solid is washed with cold hexane and collected by filtration to yield 1.5 g (29%) of the title compound as white platelets, m.p. 52°-54° C.

Workup

  1. customThe ice bath is removed
  2. additionEther (200 mL) and 1.5 N HCl (130 mL) are added
  3. stirringthe resulting two-phase mixture is stirred vigorously (4.5 hours, 25° C.)
  4. customThe layers are separated
  5. washthe organic layer is washed with saturated sodium bicarbonate (2×130 mL)
  6. washwashed with brine (1×130 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue is chromatographed on silica (90:10 hexane:ethyl acetate)
  10. concentrationconcentrated in vacuo
  11. washThe resulting solid is washed with cold hexane
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-8f86aadc7b744450bb01b6eae0b08bb5
Source dataset
uspto-grants-1992_11
Patent number
US05162360

Reaction notes

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