Pyridine → (E)-3,7-dimethylocta-2,6-dienyl 2-chloroacetate

HRID 922003Notes

Reaction equation

HRID 922003 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6]/[C:7](=[CH:9]/[CH2:10][OH:11])/[CH3:8])[CH3:3].[C:12]1(=[O:18])OC(=O)C[CH2:13]1.N1C=CC=CC=1.[Cl:25]CCl>CN(C1C=CN=CC=1)C>[Cl:25][CH2:13][C:12]([O:11][CH2:10]/[CH:9]=[C:7](\[CH3:8])/[CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])=[O:18]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7922Succinic anhydrideHCID 637566Geraniol

Product 1

HCID 5890636(E)-3,7-dimethylocta-2,6-dienyl 2-chloroacetateYield 99%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Geraniol [1] (1.542 g, 10 mmol), succinic anhydride (1.201 g, 12 mmol) and 4-DMAP (10 mg, cat) were suspended in anhydrous dichloromethane (50 ml) under an atmosphere of dry nitrogen. Pyridine (0.791 g, 10 mmol) was added and the reaction mixture was stirred for 24 hrs at room temperature. The reaction mixture was successively washed with 2N HCl and H2O, dried over Na2SO4 and the solvent was evaporated. Remaining volatile material was removed under reduced pressure (0.01 mbar) to yield product [2] as yellow liquid in 99% yield. The product was pure according to 1H NMR and directly subjected to the next step without further purification. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=12.24 (br s, 1H), 5.29 (t, J=7.0 Hz, 1H), 5.08 (t, 6.7, 1H), 4.55 (d, J=7.1 Hz, 2H), 2.49 (m, 2H), 2.03 (m, 4H), 1.67 (s, 3H), 1.66 (s, 3H), 1.59 (s, 3H). 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=173.3, 172.2, 141.2, 131.1, 123.7, 118.5, 60.7, 38.9, 28.7, 28.6, 25.8, 25.5, 17.5, 16.1.

Workup

  1. washThe reaction mixture was successively washed with 2N HCl and H2O
  2. dry with materialdried over Na2SO4
  3. customthe solvent was evaporated
  4. customwas removed under reduced pressure (0.01 mbar)

Sources & evidence

ORD record
ord-674ce5d74402447086dba0a2fdb40a37
Source dataset
uspto-grants-2016_03
Patent number
US09278134B2

Reaction notes

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