Hydrochloric Acid → 1-Methoxy-4-(1-methylethenyl)benzene

HRID 392550Notes

Reaction equation

HRID 392550 reaction equation
C[Mg]Br.[CH2:4](OCC)C.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=O)[CH3:18])=[CH:13][CH:12]=1.Cl>C(OCC)C>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:18])=[CH2:4])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 74764'-MethoxyacetophenoneHCID 178467822HCID 178467822, compound

Product 1

HCID 2594141-Methoxy-4-(1-methylethenyl)benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a 1000 mL three-necked flask equipped with a mechanical stirrer, methyl magnesium bromide/diethyl ether solution (200 mL, 3.0 mol) is added. A solution of 85.3 g of 4′-methoxy-acetophenone dissolved in 80 mL of anhydrous diethyl ether is charged to the Grignard reagent over 90 minutes at ambient temperature. Diethyl ether (200 mL) and 250 mL of 3N hydrochloric acid are added slowly to the reaction mixture. The solution is stirred for another 30 minutes. The aqueous layer is separated and washed twice with 100 mL of diethyl ether. The ethereal layers are combined and vacuum distilled. The desired product is obtained in a yield of 91.7 g as a yellow oil whose structure is verified by 1Hnmr and mass spectroscopy.

Workup

  1. customTo a 1000 mL three-necked flask equipped with a mechanical stirrer
  2. customThe aqueous layer is separated
  3. washwashed twice with 100 mL of diethyl ether
  4. distillationvacuum distilled

Sources & evidence

ORD record
ord-c3c4cde8356b49bb88c14ecf0ba94844
Source dataset
uspto-grants-2004_10
Patent number
US06800676B2

Reaction notes

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