Maleic Anhydride → 4-(4,8-Dimethyl-3,7-nonadienyl) cyclohex-4-ene-1,2-dioic anhydride

HRID 464051Notes

Reaction equation

HRID 464051 reaction equation
[CH3:1][CH2:2][C:3]([CH2:5][CH2:6]/[CH:7]=[C:8](/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])\[CH3:9])=[CH2:4].[C:16]1(=[O:22])[O:21][C:19](=[O:20])[CH:18]=[CH:17]1>C(Cl)(Cl)(Cl)Cl>[CH3:9][C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:14])[CH3:15])=[CH:7][CH2:6][CH2:5][C:3]1[CH2:4][CH:17]2[C:16](=[O:22])[O:21][C:19](=[O:20])[CH:18]2[CH2:1][CH:2]=1

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 15228937beta Farnesene2×

Product 1

HCID 537099904-(4,8-Dimethyl-3,7-nonadienyl) cyclohex-4-ene-1,2-dioic anhydride

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The (E)-β-farnesene-containing product of Example 1 (6.0 g) and maleic anhydride (2.0 g) in carbon tetrachloride (20 ml) are reacted together at 25° C. for 2 hours. The mixture is then distilled under reduced pressure to give 4-(4,8-dimethyl-3,7-nonadienyl) cyclohex-4-ene-1,2-dioic anhydride as a yellow oil (3.5, 70%; b.p.176°-182° C./0.25τ; nD20 1.5907; M+ (m/z as % base peak): 302 (2.3): δ(CCl4) 1.70 (m, 9H), 2.08 (m, 8H, 2.20-2.70 (m, 4H), 3.36 (m, 2H), 5.16 (m, 2H), 5.70 (br, t, 1H).

Workup

  1. customare reacted together at 25° C. for 2 hours
  2. distillationThe mixture is then distilled under reduced pressure

Sources & evidence

ORD record
ord-1b9a602cbda843448d72266ed2e8ed76
Source dataset
uspto-grants-1985_10
Patent number
US04546110

Reaction notes

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