9,10,16-Trihydroxyhexadecanoic acid → Heptanal, 7-hydroxy-

HRID 2052315Notes

Reaction equation

HRID 2052315 reaction equation
[OH-].[Na+].C(CCCC(O)=O)CCCC(O)[CH:8]([OH:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15].[Na].I([O-])(=O)(=O)=O.[Na+].C(=O)(O)[O-].[Na+]>O.ClCCl>[OH:16][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[O:15]

Participants

8

Reactant 5

HCID 107909,10,16-Trihydroxyhexadecanoic acidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 23667635Sodium periodate

Product 1

HCID 11007931Heptanal, 7-hydroxy-Yield 100.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

Sodium hydroxide (13.2 g.) in water (660 ml.) was added to aleuritic acid (100 g.) and the suspension stirred at 0° to 10° C. To the resulting suspension of sodium aleuritate was added sodium periodate (80 g.) in water (800 ml.) over 1 hour, without allowing the temperature to rise above 15° C. Dichloromethane (200 ml.) was then added and the mixture stirred for a further 2.5 hours at 15° C. A further amount of dichloromethane (300 ml.) and saturated aqueous sodium bicarbonate (100 ml.) were added and the mixture vigorously stirred. The precipitated sodium iodate was removed by filtration and the dichloromethane layer separated. The aqueous phase was washed with dichloromethane (500 ml.) and the combined dichloromethane extracts dried over anhydrous magnesium sulphate. Removal of the dichloromethane in vacuo below 40° C. gave 7-hydroxyheptanal (43 g.), νmax 3400 cm-1, 2700 cm-1, 1710 cm -1.

Workup

  1. customto rise above 15° C
  2. stirringthe mixture stirred for a further 2.5 hours at 15° C
  3. stirringthe mixture vigorously stirred
  4. customThe precipitated sodium iodate was removed by filtration
  5. customthe dichloromethane layer separated
  6. washThe aqueous phase was washed with dichloromethane (500 ml.)
  7. dry with materialthe combined dichloromethane extracts dried over anhydrous magnesium sulphate
  8. customRemoval of the dichloromethane in vacuo below 40° C.

Sources & evidence

ORD record
ord-b649a9aa165047a181009f59abfd13a5
Source dataset
uspto-grants-1980_01
Patent number
US04183870

Reaction notes

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