Octadecanoic acid, 1,1'-anhydride → Matairesinol stearate

HRID 490783Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C@@H:11]2[C@@H:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([OH:26])=[C:22]([O:24][CH3:25])[CH:23]=3)[C:14](=[O:15])[O:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[OH:9].[C:27]([O:46]C(=O)CCCCCCCCCCCCCCCCC)(=[O:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C@@H:11]2[C@@H:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([OH:26])=[C:22]([O:24][CH3:25])[CH:23]=3)[C:14](=[O:15])[O:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[OH:9].[C:27]([O-:46])(=[O:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

Conditions

Temperature: 65 °C

Procedure

Matairesinol (500 mg, 1.4 mmol) was dissolved in 25 ml pyridine. To the solution stearic acid anhydride (3.1 g, 5.6 mmol) was added in small portions. The temperature was raised to 65° C. and the mixture was stirred for 24 h. The solvent was removed under reduced pressure and the residue dissolved in dichloromethane. Unreacted stearic anhydride and stearic acid precipitated from the dichloromethane solution and were filtered off. The solvent was then removed and the residue was washed with n-hexane to afford matairesinol stearate as a white solid. Yield 514 mg, 41%. Purity approximately 90%, consisting of some free stearic acid and acid anhydride (NMR).

Workup

customThe solvent was removed under reduced pressure
dissolutionthe residue dissolved in dichloromethane
customprecipitated from the dichloromethane solution
filtrationwere filtered off
customThe solvent was then removed
washthe residue was washed with n-hexane

Sources & evidence

ORD record: ord-13e1612062ca4308948fb1b75f011120
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528166B2

Reaction notes

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