Ethanol → Ethyl 3,3-dimethylacrylate

HRID 1068551Notes

Reaction equation

HRID 1068551 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4]([OH:6])=[O:5].[CH2:8](O)[CH3:9]>>[CH3:1][C:2]([CH3:7])=[CH:3][C:4]([O:6][CH2:8][CH3:9])=[O:5]

Participants

3

Reactant 2

HCID 702EthanolHCID 109313-Methyl-2-butenoic acid

Product 1

HCID 12516Ethyl 3,3-dimethylacrylate

Procedure

Ten grams 3,3-dimethylacrylic acid was dissolved in 100 ml absolute ethanol and 0.5 ml concentrated (37% approx.) hydrochloric acid added. The reaction mix was refluxed for 24 to 48 hours with a Dean-Stark trap filled with activated molecular sieves inserted between the reaction vessel and the condenser. After cooling, the solvent was removed by rotary evaporation under reduced pressure at 50° C. to yield 6.3 g of a cloudy, yellow oil (ethyl 3-methyl-2-butenoate.)

Workup

  1. concentration0.5 ml concentrated (37% approx.) hydrochloric acid
  2. additionadded
  3. additionThe reaction mix
  4. temperaturewas refluxed for 24 to 48 hours with a Dean-Stark trap
  5. additionfilled with activated molecular sieves
  6. temperatureAfter cooling
  7. customthe solvent was removed by rotary evaporation under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-28f181355e274991975d17dba3e66eff
Source dataset
uspto-grants-2001_06
Patent number
US06251832B1

Reaction notes

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