Propionic Acid → HCID 21030583, compound

HRID 1829595Notes

Reaction equation

HRID 1829595 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl[CH2:8][C:9]([O:11][C:12]([CH:15]1[CH2:20][CH2:19][CH2:18][C:17]([CH3:22])([CH3:21])[CH2:16]1)([CH3:14])[CH3:13])=[O:10].[C:23]([OH:27])(=[O:26])[CH2:24][CH3:25].CCOCC>CC(C)=O>[C:23]([O:27][CH2:8][C:9]([O:11][C:12]([CH:15]1[CH2:20][CH2:19][CH2:18][C:17]([CH3:22])([CH3:21])[CH2:16]1)([CH3:14])[CH3:13])=[O:10])(=[O:26])[CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 1032Propionic AcidHCID 3283Diethyl EtherHCID 11430Potassium Carbonate2×HCID 858714801-(3,3-Dimethylcyclohexyl)-1-methylethyl chloroacetate

Product 1

HCID 21030583HCID 21030583, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

K2CO3 (6.2 g, 45 mmol) and 1-(3,3-dimethylcyclohexyl)-1-methylethyl chloroacetate (2,5 g, 10 mmol) are added successively to a solution of propionic acid (1.8 g, 30 mmol) in acetone (20 ml). After the suspension has been heated under reflux for 36 hours, it is allowed to cool and ether (80 ml) and 10% K2CO3 solution (50 ml) are added. After phase separation has taken place, the aqueous phase is freed from residual acetone and the aqueous phase is also extracted twice with 50 ml diethyl ether. The combined organic phases are also washed once with water and once with saturated NaCl solution, then dried, filtered off and freed from solvent in a rotary evaporator. After purification by flash chromatography (cyclohexane/EtOAc=10:1, Rf=0.23) and subsequent bulb tube distillation, (BTD: 215° C., 0.9 mbar) 2.1 g (78%) 2-[1-(3,3-dimethylcyclohexyl)-1-methylethoxy]-2-oxoethyl propionate is obtained as a colorless liquid.

Workup

  1. temperatureAfter the suspension has been heated
  2. temperatureunder reflux for 36 hours
  3. temperatureto cool
  4. customAfter phase separation
  5. extractionthe aqueous phase is also extracted twice with 50 ml diethyl ether
  6. washThe combined organic phases are also washed once with water and once with saturated NaCl solution
  7. customdried
  8. filtrationfiltered off
  9. customfreed from solvent in a rotary evaporator
  10. customAfter purification
  11. distillationby flash chromatography (cyclohexane/EtOAc=10:1, Rf=0.23) and subsequent bulb tube distillation

Sources & evidence

ORD record
ord-a1f946354bd44dd0a286be1a60b10a21
Source dataset
uspto-grants-2006_06
Patent number
US07064102B2

Reaction notes

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