Ammonia → HCID 21388142, compound

HRID 1833940Notes

Reaction equation

HRID 1833940 reaction equation
[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)([CH3:8])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].N.[Li].[Cl-].[NH4+]>O1CCCC1.C(O)C>[CH3:8][C:2]([C:9]1[CH2:10][CH:11]=[C:12]([CH3:15])[CH2:13][CH:14]=1)([CH3:1])[CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 10878311γ,γ,4-Trimethylbenzenebutanoic acid

Product 1

HCID 21388142HCID 21388142, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a refluxing solution of 4-methyl-4-p-tolylpentanoic acid (51.5 g, 0.25 mol) in tetrahydrofuran (500 ml) and liquid ammonia (1500 ml) was added, portionwise, lithium metal (26.0 g, 3.75 gram atom). After the reaction mixture was stirred for 15 minutes, ethanol (150 ml) was added over 40 minutes. The reaction mixture was stirred an additional hour until the dark blue solution became colorless. Ammonium chloride (50 g) was added and the ammonia allowed to evaporate. The residue was acidified with HCl (pH ca. 3), extracted with ethylene dichloride, washed with water, concentrated and distilled to yield 49.6 g (80.8%) of the 4-methyl-4-(4-methyl-1,4-cyclohexadien-1-yl)pentanoic acid: bp 128° -130° C (1 mm); nD20 1.4955; λmax 211 nm; δTMSCDCl3 11.21 (s,1), 5.43-5.50 (broad band, 2) 2.62 (s,4), 1.66 (s,3) 1.03 (s, 6H).

Workup

  1. stirringThe reaction mixture was stirred an additional hour until the dark blue solution
  2. customto evaporate
  3. extractionextracted with ethylene dichloride
  4. washwashed with water
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-1c486bb45e064ce8a7cb40ccf6bf97e3
Source dataset
uspto-grants-1978_01
Patent number
US04067906

Reaction notes

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