Citric Acid → Trihexadecyl citrate

HRID 650459Notes

Reaction equation

HRID 650459 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5]([OH:7])=[O:6])[OH:4].I[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CN(C)C=O>[CH2:15]([O:10][C:9](=[O:11])[CH2:8][C:3]([C:5]([O:7][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15])=[O:6])([OH:4])[CH2:2][C:1]([O:13][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15])=[O:12])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 110071-Iodohexadecane

Product 1

HCID 6452032Trihexadecyl citrateYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene(1,5-5)(4.567 g, 30 mmol) was added at room temperature to a solution of citric acid (1.924 g, 10 mmol) in N,N-dimethylformamide (50 ml). 1-Iodohexadecane (10.570 g, 30 mmol) was added and the resulting mixture was stirred at 50° C. for 21 hours. The precipitated product was filtered off and washed with N,N-dimethylformamide and the crude product was purified by flash chromatography on silica gel using chlorform/hexane for elution. Yield: 83%. 1H-NMR (300 MHz, CDCl3): δ 088(t,9H), 1.26(m,78H), 1.60(m,6H), 2.84(q,4H), 4.07(t,4H), 4.13(s,1H), 4.20(t,2H). FAB-MS: 887.6(M+Na).

Workup

  1. filtrationThe precipitated product was filtered off
  2. washwashed with N,N-dimethylformamide
  3. customthe crude product was purified by flash chromatography on silica gel
  4. washfor elution

Sources & evidence

ORD record
ord-ff189f389c904730b5eb2a8bd1af6d48
Source dataset
uspto-grants-2001_08
Patent number
US06274120B1

Reaction notes

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