Ethyl Acetate → 2-Ethyl-3-hydroxy-4-ethoxycarbonylbut-1-ene

HRID 435067

Reaction equation

HRID 435067 reaction equation
[Li].[C:2]([O:5][CH2:6][CH3:7])(=[O:4])[CH3:3].[CH:8]([C:10]([CH2:12][CH3:13])=[CH2:11])=[O:9].[Cl-].[NH4+]>N.C(OCC)C>[CH2:12]([C:10]([CH:8]([OH:9])[CH2:3][C:2]([O:5][CH2:6][CH3:7])=[O:4])=[CH2:11])[CH3:13]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 70203EthylacroleinHCID 3028194Lithium

Product 1

HCID 204906852-Ethyl-3-hydroxy-4-ethoxycarbonylbut-1-eneYield 23.6%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 3283Diethyl EtherSolvent

Procedure

2.2 g Lithium metal was dissolved in 200 ml of liquid ammonia containing a trace of ferric nitrate, and 21 g (23.5 ml) of ethyl acetate was added. The mixture was stirred for two minutes and 2-formylbut-1-ene (19 g) in diethyl ether (60 ml) was added over 10 minutes at the reflux temperature of the mixture. Stirring was continued for a further 30 minutes, a slight excess of ammonium chloride was added to the reaction mixture and the ammonia was evaporated off. The residue was extracted with diethyl ether, was washed with dilute hydrochloric acid and then with brine, was dried, was evaporated and was distilled at 110°-120° C./10 mm Hg to give 9.2 g (24%) of 2-ethyl-3-hydroxy-4-ethoxycarbonylbut-1-ene (approximately 90% pure).

Workup

  1. additionwas added
  2. stirringStirring
  3. waitwas continued for a further 30 minutes
  4. customthe ammonia was evaporated off
  5. extractionThe residue was extracted with diethyl ether
  6. washwas washed with dilute hydrochloric acid
  7. dry with materialwith brine, was dried
  8. customwas evaporated
  9. distillationwas distilled at 110°-120° C./10 mm Hg

Sources & evidence

ORD record
ord-9473dc887f584f499a445efb3f824622
Source dataset
uspto-grants-1983_08
Patent number
US04400198

Linked notes

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