Hydrochloric Acid → HCID 14879909, compound

HRID 1709649Notes

Reaction equation

HRID 1709649 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[Mg].II.[CH2:15]=[C:16]([CH2:19]Cl)[CH2:17][Cl:18].Cl>C(OCC)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH2:19][C:16](=[CH2:15])[CH2:17][Cl:18])=[CH:3][CH:4]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 158593-Chloro-2-chloromethyl-1-propeneHCID 775951-Bromo-4-tert-butylbenzeneHCID 5462224Magnesium

Product 1

HCID 14879909HCID 14879909, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of p-bromo-(t-butyl)benzene (21.3 g., 0.10 mole) in dry diethyl ether (100 ml.) was added dropwise to a mixture of magnesium turnings (2.4 g.), a single iodine crystal and dry diethyl ether (50 ml.). The mixture was allowed to react at ambient temperature for two hours. The resultant Grignard solution was transferred to a dry dropping funnel and added dropwise to a solution of methallyl dichloride (13 8 g., 0.11 mole) in dry diethyl ether (50 ml.). After complete addition of the Grignard solution, the mixture was refluxed for three hours and thereafter cooled with an ice-water bath while 15% hydrochloric acid (150 ml.) was added thereto. The mixture was extracted with diethyl ether and the organic phase dried over sodium sulfate, filtered and evaporated to yield a liquid. The liquid was distilled to provide 10 grams of 2-[(p-t-butylphenyl)methyl]-2-propenyl chloride. This product was characterized by a boiling point of 105° C. to 111° C. at a pressure of 0.25 mm Hg.

Workup

  1. customto react at ambient temperature for two hours
  2. additionAfter complete addition of the Grignard solution
  3. temperaturethe mixture was refluxed for three hours
  4. additionwas added
  5. extractionThe mixture was extracted with diethyl ether
  6. dry with materialthe organic phase dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto yield a liquid
  10. distillationThe liquid was distilled

Sources & evidence

ORD record
ord-4e0a6e60deea4a358d4c40a7f4f4f6d3
Source dataset
uspto-grants-1990_08
Patent number
US04950671

Reaction notes

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