Ammonia → 3-(4-Oxocyclohex-1-en-1-yl)propanoic acid

HRID 1731649Notes

Reaction equation

HRID 1731649 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.N.[Li].[Cl-].[NH4+]>O1CCCC1.C(O)(C)(C)C>[O:2]=[C:3]1[CH2:8][CH2:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:5][CH2:4]1

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 957503-(p-Methoxyphenyl)propionic acidHCID 3028194Lithium

Product 1

HCID 202283473-(4-Oxocyclohex-1-en-1-yl)propanoic acid

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4.4 g of 4-methoxybenzenepropionic acid and 75 ml of tert-butanol, 50 ml of tetrahydrofuran and 300 ml of liquid ammonia there was added 0.85 g of lithium wire in 2-3 cm pieces over a 10 minute period to give a mixture which had a persistent deep blue color. After an additional 10 minutes, 13.4 g of powdered ammonium chloride was added and the ammonia was allowed to evaporate. The residue was dissolved in 300 ml of water and washed twice with 200-ml portions of ether. The aqueous mixture was acidified with concentrated hydrochloric acid and extracted thoroughly with three 200-ml portions of ether. The combined organic layers were dried over magnesium sulfate and the solvent was evaporated to give 4-oxocyclohex-1-enepropionic acid as a clear oil. 1H NMR (CDCl3) δ 2.20-2.80 (br m, 20H); 5.45 (m, 1H); 11.3 (br s, 1H).

Workup

  1. customto give a mixture which
  2. customto evaporate
  3. dissolutionThe residue was dissolved in 300 ml of water
  4. washwashed twice with 200-ml portions of ether
  5. extractionextracted thoroughly with three 200-ml portions of ether
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3871b901985a4ffd923e0ca2eba0a1a6
Source dataset
uspto-grants-1986_11
Patent number
US04622422

Reaction notes

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