Succinic anhydride → Digeranyl Succinate

HRID 1599975Notes

Reaction equation

HRID 1599975 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6]/[C:7](=[CH:9]/[CH2:10][OH:11])/[CH3:8])[CH3:3].[OH:12][CH2:13]/[CH:14]=[C:15](/[CH3:22])\[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20].[C:23]1(=O)[O:28][C:26](=[O:27])[CH2:25][CH2:24]1>O>[C:23]([O:12][CH2:13]/[CH:14]=[C:15](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])\[CH3:22])(=[O:28])[CH2:24][CH2:25][C:26]([O:11][CH2:10]/[CH:9]=[C:7](/[CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])\[CH3:8])=[O:27]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 637566GeraniolHCID 643820Nerol

Product 1

HCID 22593555Digeranyl Succinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Synthesis (c): A mixture of geraniol and nerol (approximately 70:30 by weight) in the amount of 94.86 g (0.615 mol) and succinic anhydride in theamount of 20.51 g (0.205 mol) are combined at room temperature. The mixtureis heated to 140° C. for 6 h while water is removed using an argon sparge. After cooling to room temperature, the mixture is placed in a Kugelrohr oven and concentrated at 80°-85 ° C. for 5.5 h. Purity of the product is determined by thin layer chromatography and the structure confirmed by 13C and 1H NMR.

Workup

  1. customare combined at room temperature
  2. customis removed
  3. customsparge
  4. concentrationconcentrated at 80°-85 ° C. for 5.5 h

Sources & evidence

ORD record
ord-65b3984735d3454ebfa89d5abdd325db
Source dataset
uspto-grants-1998_04
Patent number
US05744435

Reaction notes

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