Butyl chloroformate → HCID 53895456, compound

HRID 1977536Notes

Reaction equation

HRID 1977536 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])C)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-:22])C.[K+].[CH2:25](OC(Cl)=O)[CH2:26][CH2:27][CH3:28]>C1COCC1.CCOCC>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([CH3:18])=[CH:13][O:14][C:15](=[O:22])[O:17][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 61140Butyl chloroformateHCID 23665647Potassium tert-butoxideHCID 53757095Acetic Acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl Ester

Product 1

HCID 53895456HCID 53895456, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 40.0 g acetic acid 3-(4-tert-butyl-phenyl)-2- methyl-propenyl ester in 250 ml of THF was cooled to −70° C. A solution of 25.0 g potassium-tert-butoxide in 100 ml of THF was added at −70° C. during 35 min. and the resulting reaction mixture was stirred for 60 min. at the same temperature. 23.3 g butyl-chloroformate was dropped in during 40 min. and the reaction mixture was stirred for another 90 min. 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 and purified by chromatography to yield a colorless oil.

Workup

  1. customthe resulting reaction mixture
  2. stirringthe reaction mixture was stirred for another 90 min. at −70° C
  3. washwashed with saturated NaHCO3 and brine
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. distillationdistilled
  8. custompurified by chromatography
  9. customto yield a colorless oil

Sources & evidence

ORD record
ord-17a9130549314661b83c2e7ad49881ce
Source dataset
uspto-grants-2001_05
Patent number
US06232487B1

Reaction notes

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