Toluene → Dec-9-enyl 2-allyloxy-acetate

HRID 1368703Notes

Reaction equation

HRID 1368703 reaction equation
[CH2:1]([O:4][CH2:5][C:6]([OH:8])=[O:7])[CH:2]=[CH2:3].C1(C)C=CC=CC=1.[CH2:16](O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH2:1]([O:4][CH2:5][C:6]([O:8][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=[CH2:16])=[O:7])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 256129-Decen-1-olHCID 109970062-(Prop-2-en-1-yloxy)acetic acid

Product 1

HCID 18520721Dec-9-enyl 2-allyloxy-acetateYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2.5 g of crude 2-allyloxyacetic acid are introduced into 40 ml of toluene, and 4.7 g (30 mmol) of 9-decen-1-ol and 0.38 g (2.0 mmol) of p-toluenesulfonic acid are added. The mixture is then heated with a water separator until visible amounts of water no longer separate out. The mixture is then cooled, and the organic phase is washed once with saturated NaHCO3 solution, dried over Na2SO4 and filtered, and the product is freed from the solvent. Flash chromatography (cyclohexane/EtOAc=20:1, Rf=0.29) gives 3.1 g (62%) of dec-9-enyl 2-allyloxy-acetate as a colorless oil.

Workup

  1. additionare added
  2. customno longer separate out
  3. temperatureThe mixture is then cooled
  4. washthe organic phase is washed once with saturated NaHCO3 solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-d2a71ead6cf243f39298699a76fa7ec4
Source dataset
uspto-grants-2003_06
Patent number
US06573391B1

Reaction notes

Loading…