Hydrochloric Acid → But-2-enoic acid 1,2-dimethyl-propyl ester

HRID 1627977Notes

Reaction equation

HRID 1627977 reaction equation
[C:1](Cl)(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[CH3:7][CH:8]([CH3:12])[CH:9]([OH:11])[CH3:10].C(N(C(C)C)CC)(C)C.Cl>ClCCl>[CH3:10][CH:9]([O:11][C:1](=[O:5])[CH:2]=[CH:3][CH3:4])[CH:8]([CH3:12])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 117323-Methyl-2-butanolHCID 81531DiisopropylethylamineHCID 643131trans-Crotonyl chloride

Product 1

HCID 86762524But-2-enoic acid 1,2-dimethyl-propyl esterYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Crotonoyl chloride (21.35 g) in dichloromethane (100 mL) was charged into a 2-L reaction flask and cooled to 0° C. 3-Methyl-butan-2-ol (18 g) was added followed by diisopropylethylamine (31.7 g). The reaction mixture was aged at 0-10° C. for about 30 minutes and poured into dilute hydrochloric acid (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-2-enoic acid 1,2-dimethyl-propyl ester (25.6 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-24f0a407cccb4dd399da305d911477cd
Source dataset
uspto-grants-2014_07
Patent number
US08785677B1

Reaction notes

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