Benzenepropanoyl chloride → 3-Phenyl-propionic acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl ester

HRID 1533693Notes

Reaction equation

HRID 1533693 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([CH3:18])=[CH:13][O:14][C:15](=[O:17])[CH3:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[C:25]1([CH2:31]CC(Cl)=O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1.CCOCC>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([CH3:18])=[CH:13][O:14][C:15](=[O:17])[CH2:16][CH2:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 64801Benzenepropanoyl chlorideHCID 23665647Potassium tert-butoxideHCID 53757095Acetic Acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl Ester

Product 1

HCID 537449663-Phenyl-propionic acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl esterYield 83.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 65.8 g acetic acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl ester in 200 ml of THF was cooled to −70° C. A solution of 42.3 g potassium-tert-butoxide in 200 ml of THF was added at −70° C. during 20 min. and the resulting reaction mixture was stirred for 90 min. at the same temperature. 53.5 g 3-phenyl-propionyl chloride was dropped in and the reaction mixture was stirred for another 3 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 thin-layer distilled to yield 75.0 g of a yellow oil.

Workup

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

Sources & evidence

ORD record
ord-7a9dfa2724414b4fb1a7cb91e5a3c90f
Source dataset
uspto-grants-2001_03
Patent number
US06207857B1

Reaction notes

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