Toluene → HCID 131732701, compound

HRID 1468253Notes

Reaction equation

HRID 1468253 reaction equation
[C:1]([O:9]CC)([O:6][CH2:7][CH3:8])(OCC)[CH3:2].[CH2:12]([CH:14](CCCC)C(O)=O)[CH3:13].[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH:22]1(/[CH:28]=[C:12](\[CH3:14])/[CH2:13][CH2:2][C:1]([O:6][CH2:7][CH3:8])=[O:9])[CH2:27][CH2:26][CH:25]=[CH:24][CH2:23]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 86972-Ethylhexanoic AcidHCID 66221Triethyl orthoacetate

Product 1

HCID 131732701HCID 131732701, compound

Conditions

Temperature
200 °C

Procedure

The following reagents were charged in a stainless steel autoclave: above-obtained alcohol (9.5 g; 62.4 mmol); triethyl orthoacetate (23.14 g; 140 mmol); 2-ethylhexanoic acid (0.24 g; 1.7 mmol) and toluene (18 ml). The autoclave was purged with nitrogen and heated in an oil bath at 200° C. overnight. After cooling to room temperature, the reaction was poured onto water. A few drops of 5% aq. HCl were added. The mixture was extracted twice with diethyl ether. Each organic phase was washed with water, aqueous saturated NaHCO3 and brine (3×). Combined extracts were dried over sodium sulfate. The product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 9:1) followed by bulb-to-bulb distillation (120° C./0.01 mbar). The product was obtained (yield: 79%) as a 98:2 mixture of E and Z isomers.

Workup

  1. customThe autoclave was purged with nitrogen
  2. temperatureAfter cooling to room temperature
  3. additionthe reaction was poured onto water
  4. additionA few drops of 5% aq. HCl were added
  5. extractionThe mixture was extracted twice with diethyl ether
  6. washEach organic phase was washed with water, aqueous saturated NaHCO3 and brine (3×)
  7. dry with materialCombined extracts were dried over sodium sulfate
  8. customThe product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 9:1)
  9. distillationfollowed by bulb-to-bulb distillation (120° C./0.01 mbar)
  10. customThe product was obtained (yield: 79%)
  11. additionas a 98:2 mixture of E and Z isomers

Sources & evidence

ORD record
ord-141d9ba651a6466895ec3c2d88f62288
Source dataset
uspto-grants-2015_04
Patent number
US09000226B2

Reaction notes

Loading…