3-Chlorocarbonyl-propionic acid 3,7-dimethyl-oct-6-enylester → Succinic acid 3,7-dimethyl-oct-6-enyl ester 3-(3-isopropyl-phenyl)-but-1-enyl ester

HRID 1533698Notes

Reaction equation

HRID 1533698 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:10]([CH3:17])[CH:11]=[CH:12][O:13][C:14](=[O:16])[CH3:15])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[CH3:24][CH:25]([CH2:36][CH2:37][CH:38]=[C:39]([CH3:41])[CH3:40])[CH2:26][CH2:27][O:28][C:29](=[O:35])[CH2:30]CC(Cl)=O>C1COCC1.CCOCC>[CH:1]([C:4]1[CH:5]=[C:6]([CH:10]([CH3:17])[CH:11]=[CH:12][O:13][C:14](=[O:16])[CH2:15][CH2:30][C:29]([O:28][CH2:27][CH2:26][CH:25]([CH3:24])[CH2:36][CH2:37][CH:38]=[C:39]([CH3:41])[CH3:40])=[O:35])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 153907233-Chlorocarbonyl-propionic acid 3,7-dimethyl-oct-6-enylesterHCID 23665647Potassium tert-butoxideHCID 54258447Acetic acid 3-(3-isopropyl-phenyl)-but-1-enyl ester

Product 1

HCID 69826323Succinic acid 3,7-dimethyl-oct-6-enyl ester 3-(3-isopropyl-phenyl)-but-1-enyl esterYield 50.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7.60 g acetic acid 3-(3-isopropyl-phenyl)-but-1-enyl ester in 50 ml of THF was cooled to −70° C. A solution of 5.00 g potassium-tert-butoxide in 50 ml of THF was added at 70° C. and the resulting reaction mixture was stirred for 2 hours at the same temperature. 11.20 g 3-chlorocarbonyl-propionic acid 3,7-dimethyl-oct-6-enyl ester was then dropped in and the reaction mixture was stirred for another 2 hours at −70° C. Then the reaction mixture was diluted with ether, washed with saturated NaHCO3 and brine. The organic phase was dried, filtered and evaporated to dryness. The residue was purified by chromatography to yield 7.10 g of a yellow oil.

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred for another 2 hours at −70° C
  3. washwashed with saturated NaHCO3 and brine
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-419867b5849e48699a4cc19f51dd823a
Source dataset
uspto-grants-2001_03
Patent number
US06207857B1

Reaction notes

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