Diethyl Ether → HCID 19764336, compound

HRID 1885464Notes

Reaction equation

HRID 1885464 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C=[CH:8][CH2:9][CH2:10][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][CH2:24][CH2:25][CH:26]([C:32]([O:34]CC)=O)[C:27]([O:29]CC)=O.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH3:54]COCC>>[CH2:54]=[C:24]([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH3:8])[CH2:25][CH:26]([CH2:27][OH:29])[CH2:32][OH:34]

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 1317175182-(Methyleneoctadecyl)propanedioic acid, diethyl ester

Product 1

HCID 19764336HCID 19764336, compound

Procedure

A solution of 1.03 g of lithium aluminum hydride in 50 ml of ether is cooled in a water bath. A mixture of 6.78 g of 2-(methyleneoctadecyl)propanedioic acid, diethyl ester in 50 ml of ether is added. This mixture is stirred at reflux for 2 hours, then overnight at room temperature and finally at reflux for 4 hours. The mixture is stirred with sodium sulfate decahydrate, then filtered and recrystallized from ethyl acetate/hexane, to give 4.87 g of the desired compound as white crystals, mp. 64°-65° C.

Workup

  1. additionis added
  2. temperatureat reflux for 2 hours
  3. filtrationfiltered
  4. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-32a32fa1c6d9446ba16339edb20819c6
Source dataset
uspto-grants-1992_09
Patent number
US05144045

Reaction notes

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