Hydrochloric Acid → 1-(But-2-yn-1-yl)cyclobutane-1-carboxylic acid

HRID 893373Notes

Reaction equation

HRID 893373 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].C(NC(C)C)(C)C.[CH:13]1([C:19]([OH:21])=[O:20])[CH2:18][CH2:17][CH2:16]CC1.BrCC#CC.Cl>CCCCCC.O1CCCC1>[CH3:4][C:3]#[C:2][CH2:1][C:13]1([C:19]([OH:21])=[O:20])[CH2:16][CH2:17][CH2:18]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7413Cyclohexanecarboxylic acidHCID 7912DiisopropylamineHCID 27568621-Bromo-2-butyneHCID 178418339Butyllithium

Product 1

HCID 132455971-(But-2-yn-1-yl)cyclobutane-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-10 °C

Procedure

At -30° C., 265 ml of 1.66-molar butyllithium solution in hexane is added to a solution of 44.52 g of diisopropylamine in 200 ml of tetrahydrofuran, and thereafter 20.02 g of cyclohexanecarboxylic acid is added thereto. The mixture is stirred for 30 minutes at -10° C. and then 31.92 g of 1-bromo-2-butyne is added dropwise and the mixture is agitated for 16 hours at 25° C. whereupon it is poured on 600 ml of ice water. After acidifying with 2N hydrochloric acid to pH 4, the mixture is extracted with ether, the extract is washed with brine, dried over magnesium sulfate, and the the evaporated under vacuum. The residue is purified by distillation, thus obtaining 18 g of 2,2-trimethylenehex-4-ynoic acid (bp 140° C.-143° C., 15 torr).

Workup

  1. stirringthe mixture is agitated for 16 hours at 25° C. whereupon it
  2. extractionthe mixture is extracted with ether
  3. washthe extract is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe the evaporated under vacuum
  6. distillationThe residue is purified by distillation

Sources & evidence

ORD record
ord-b326fb7f574e4946baf55a4e87de624a
Source dataset
uspto-grants-1992_06
Patent number
US05124343

Reaction notes

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