Hydrochloric Acid → HCID 67049231, compound

HRID 1050665Notes

Reaction equation

HRID 1050665 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[Li].[Cl:7][C:8]1[CH:24]=[CH:23][C:11]([CH2:12][C:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=O)=[CH:10][CH:9]=1.Cl.CCCCCC>C1COCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][C:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[C:2]2[CH:1]=[CH:5][CH:4]=[CH:3]2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 11097890bis(4-chlorobenzyl)ketoneHCID 66906458HCID 66906458, compound

Product 1

HCID 67049231HCID 67049231, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Under a nitrogen atmosphere, a 100-mL three-necked flask was charged with 0.66 g (9.22 mmol) of lithium cyclopentadiene and 10 mL of dehydrated THF, and the mixture was stirred. This solution was cooled (to −78° C.) in a dry ice/methanol bath, and 2.50 g (8.96 mmol) of bis(4-chlorobenzyl)ketone dissolved in 15 mL of dehydrated THF was added dropwise. Subsequently, the mixture was stirred for 17 hours while gradually warming to room temperature. Then, 1 N hydrochloric acid was added to the resulting brown-black solution to terminate the reaction. Thereafter, hexane was added to perform liquid-liquid phase separation, and the aqueous layer was subjected to extraction with hexane twice. The resultant was combined with the organic layer obtained previously. The resultant liquid was then washed two times with a saturated aqueous solution of sodium hydrogen carbonate, two times with water, and once with saturated brine, and dried over magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography to obtain a target product as a yellow powder (yield 0.65 g (22%)). The target product was identified by 1H-NMR.

Workup

  1. additionwas added dropwise
  2. stirringSubsequently, the mixture was stirred for 17 hours
  3. temperaturewhile gradually warming to room temperature
  4. customto terminate
  5. customthe reaction
  6. customliquid-liquid phase separation
  7. extractionthe aqueous layer was subjected to extraction with hexane twice
  8. customobtained previously
  9. washThe resultant liquid was then washed two times with a saturated aqueous solution of sodium hydrogen carbonate, two times with water
  10. dry with materialonce with saturated brine, and dried over magnesium sulfate
  11. distillationThe solvent was distilled off
  12. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-008d7a02e5da43639a13a5e45e1ee64c
Source dataset
uspto-grants-2016_07
Patent number
US09382356B2

Reaction notes

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