Metaperiodic acid → HCID 13608882, compound

HRID 638411Notes

Reaction equation

HRID 638411 reaction equation
I(O)(=O)(=O)=O.[Cl:6][CH2:7][C:8]([OH:25])([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])CO.C(OCC)(=O)C.CCCCCC>CCOCC>[Cl:6][CH2:7][C:8](=[O:25])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 65185Metaperiodic acidHCID 13226350HCID 13226350, compound2×HCID 21226206Ethyl acetate hexane

Product 1

HCID 13608882HCID 13608882, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Periodic acid (excess) was added to a solution of 2-chloromethylhexadecan-1,2-diol (23a, 0.021 g, 0.068 mmole) in wet ether (15 ml). The progress of the reaction was followed by TLC (30% ethyl acetate-hexane) and within 70 minutes, the diol 23a was completely transformed to a new, nonpolar product. Additional ether (15 ml) was added and the organic solution was washed with water (2×) and brine. The ether layer was dried (MgSO4), filtered, and concentrated, leaving 0.017 g (0.062 mmole, 91%) of a crystalline material. Recrystallization from methanol gave 0.009 g of 1-chlorohexadecan-2-one (25), mp. 52.5°-53.5° C. (lit.16 mp., 52°-52.5° C.).

Workup

  1. washthe organic solution was washed with water (2×) and brine
  2. dry with materialThe ether layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c6f9ad81e4a44a14b931aa404a221710
Source dataset
uspto-grants-1985_12
Patent number
US04560811

Reaction notes

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