Water → Dilauryl Ether

HRID 1987311Notes

Reaction equation

HRID 1987311 reaction equation
O[C:2]1[CH:11]=[C:10](C(OC)=O)[C:9](O)=[CH:8][C:3]=1[C:4](OC)=O.Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[C:30](=[O:33])([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:18]([O:33][CH2:30][CH2:11][CH2:2][CH2:3][CH2:4][CH2:2][CH2:11][CH2:10][CH2:9][CH2:8][CH2:3][CH3:4])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 89191-BromododecaneHCID 11430Potassium CarbonateHCID 8209711,4-Benzenedicarboxylic acid, 2,5-dihydroxy-, 1,4-dimethyl ester

Product 1

HCID 20667Dilauryl EtherYield 280.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethyl 2,5-dihydroxyterephthalate (5.00 g), bromododecane (11.6 g) and anhydrous potassium carbonate (7.63 g) were reacted in N,N′-dimethylformamide at 120° C. under nitrogen for six hours. The solution was cooled and poured into water. After filtration and washing, 11.0 g of the di-dodecyl ether was obtained. This was hydrolyzed with sodium hydroxide to the diacid salt, acidified and the diacid chloride formed by reaction of 6.6 g of the diacid with a 100% molar excess of thionyl chloride. The acid chloride was added over 30 minutes to a solution of glycidol (2.0 g) and triethylamine (2.56 g) in dry toluene maintained at −10° C. Reaction was continued for 5 hours at 20° C. after which the reaction mixture was extracted with dichloromethane and water and the dichloromethane layer dried over sodium sulfate, filtered and the solvent removed under vacuum. The resulting solid was recrystallized from ethyl acetate to give 2.4 g of a pale yellow solid melting at 66-68° C., the diglycidyl ester of 2,5-didodecyloxyterephthalic acid.

Workup

  1. temperatureThe solution was cooled
  2. filtrationAfter filtration
  3. washwashing

Sources & evidence

ORD record
ord-c4321bd4848840aaab8e915fa9d23e58
Source dataset
uspto-grants-2009_06
Patent number
US07550522B2

Reaction notes

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