Hydrochloric Acid → HCID 86741246, compound

HRID 980927Notes

Reaction equation

HRID 980927 reaction equation
[Cl:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](Cl)=[O:4].[I:12][CH2:13][C:14]#[C:15]O.Cl.C(=O)(O)[O-:19].[Na+]>C1(C)C=CC=CC=1.CCOCC.C(N(CC)CC)C>[I:12][CH:13]([O:4][C:3](=[O:19])[CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[Cl:1])[C:14]#[CH:15]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 102902Chloro(phenyl)acetyl chlorideHCID 516892Sodium BicarbonateHCID 223214363-Iodopropynol

Product 1

HCID 86741246HCID 86741246, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

24.6 g of alpha-chlorophenylacetic acid chloride, dissolved in 20 ml of toluene, were added dropwise to a mixture of 23.7 g of 3-iodopropynol, 15 g of triethylamine and 100 ml of toluene. The reaction temperature was 60° C. The reaction mixture was finally taken up in 100 ml of ether and the ethereal solution was subsequently extracted first with 1N hydrochloric acid and then with saturated sodium bicarbonate solution. Finally, the organic phase was dried with sodium sulfate. After distilling off the ether, 36.5 g, corresponding to 84% of the theoretical yield, of alpha-chlorophenylacetic acid iodopropargyl ester were obtained.

Workup

  1. customwas 60° C
  2. dry with materialFinally, the organic phase was dried with sodium sulfate
  3. distillationAfter distilling off the ether, 36.5 g

Sources & evidence

ORD record
ord-3b90e789197e48ef887e9014244dfcb7
Source dataset
uspto-grants-1987_01
Patent number
US04639541

Reaction notes

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