Hydrochloric Acid → Ethyl (2-iodobenzoyl)acetate

HRID 986234Notes

Reaction equation

HRID 986234 reaction equation
C1(NC(C)C)CCCCC1.C([Li])CCC.[I:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20].Cl.[C:27]([O:30][CH2:31][CH3:32])(=[O:29])[CH3:28]>O1CCCC1.CCCCCC>[I:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([CH2:28][C:27]([O:30][CH2:31][CH3:32])=[O:29])=[O:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 62386CyclohexylisopropylamineHCID 691122-Iodobenzoyl chlorideHCID 178418339Butyllithium

Product 1

HCID 4143714Ethyl (2-iodobenzoyl)acetateYield 71.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Cyclohexyl isopropylamine (10.6 grams) is dissolved in 80 ml of tetrahydrofuran and the solution is cooled to -78° C. In a nitrogen stream, a solution of n-butyl lithium (about 15%) in hexane solution (26 ml) is added thereto, and the mixture temperature is raised to -40° C. Then it is cooled to -78° C. once again, 3.3 grams of ethyl acetate is gradually added thereto and, ten minutes thereafter, a solution of 10 grams of o-iodobenzoyl chloride in tetrahydrofuran is dropped thereinto gradually. The mixture is stirred at -78° C. for one hour, then gradually warmed up to 0° C. within two to three hours, 20 ml of 20% hydrochloric acid solution is added thereto, the mixture is poured into ice water, and extracted with ether. The extract is washed with a saturated aqueous solution of sodium bicarbonate, dried with anhydrous magnesium sulfate, ether is evaporated therefrom, and the resulting oil is purified by distilling in vacuo to give 8.5 grams of pale yellow oil, b.p. 142° C./3 mmHg.

Workup

  1. temperaturethe mixture temperature is raised to -40° C
  2. temperatureThen it is cooled to -78° C. once again
  3. temperaturegradually warmed up to 0° C. within two to three hours
  4. extractionextracted with ether
  5. washThe extract is washed with a saturated aqueous solution of sodium bicarbonate
  6. dry with materialdried with anhydrous magnesium sulfate, ether
  7. customis evaporated
  8. customthe resulting oil is purified
  9. distillationby distilling in vacuo

Sources & evidence

ORD record
ord-e28b9372110640a8a75bd3ca316b6df7
Source dataset
uspto-grants-1987_12
Patent number
US04711898

Reaction notes

Loading…