Hydrochloric Acid → But-3-enoic acid 1-ethyl-2-methyl-propyl ester

HRID 1627976Notes

Reaction equation

HRID 1627976 reaction equation
[C:1](Cl)(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[CH3:7][CH:8]([CH:10]([OH:13])[CH2:11][CH3:12])[CH3:9].C(N(C(C)C)CC)(C)C.Cl>ClCCl>[CH2:11]([CH:10]([O:13][C:1](=[O:5])[CH2:2][CH:3]=[CH2:4])[CH:8]([CH3:9])[CH3:7])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 112642-Methylpentan-3-olHCID 81531DiisopropylethylamineHCID 643131trans-Crotonyl chloride

Product 1

HCID 86762532But-3-enoic acid 1-ethyl-2-methyl-propyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Crotonoyl chloride (21.5 g) in dichloromethane (CH2Cl2) (100 mL) was charged into a 2-L reaction flask and cooled to 0° C. 2-Methyl-pentan-3-ol (prepared as above in EXAMPLE IV) (21 g) was added followed by diisopropylethylamine (31.9 g). The reaction mixture was aged at about 0-10° C. for about 30 minutes and poured into dilute hydrochloric acid (HCl) (33 g in 170 g water). Hexanes were added and the aqueous and organic layers were split. The organic layer was separated and subsequently purified via liquid chromatography to provide but-3-enoic acid 1-ethyl-2-methyl-propyl ester (28 g).

Workup

  1. customthe aqueous and organic layers were split
  2. customThe organic layer was separated
  3. customsubsequently purified via liquid chromatography

Sources & evidence

ORD record
ord-d9c1f992ac4d4969b21a50c7c216af0b
Source dataset
uspto-grants-2014_07
Patent number
US08785677B1

Reaction notes

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