Water → 1-Ethyl-4-methoxybenzene

HRID 541168Notes

Reaction equation

HRID 541168 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1)#[CH:2].O>C(OCC)(=O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 2510201-Ethynyl-4-methoxybenzene

Product 1

HCID 736901-Ethyl-4-methoxybenzeneYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

64.8 μL (0.50 mmol) of 4-ethynyl-1-methoxybenzene (12), 270 μL (15 mmol) of distilled water and stainless steel balls (50 pieces) were placed in the vessel of the planetary ball mill, which was then closed, and agitated by operating the planetary ball mill for 12 hours at 800 rpm (reversed every 30 minutes). After the lapse of 12 hours, 10 mL of ethyl acetate was added to the vessel of the ball mill to provide a solution containing the reaction mixture, which was then filtered with celite. The operation was repeated 5 times to provide a filtrate, which was then concentrated, thereby providing 47.0 mg (0.35 mmol) of 4-ethyl-1-methoxybenzene (13). The yield was 69%. The reaction is expressed by the following scheme.

Workup

  1. customwas then closed
  2. customfor 12 hours
  3. customto provide a solution
  4. additioncontaining the reaction mixture, which
  5. filtrationwas then filtered with celite
  6. customto provide a filtrate, which
  7. concentrationwas then concentrated

Sources & evidence

ORD record
ord-38cf01df55b84d2f9c1db7c17f7421e9
Source dataset
uspto-grants-2014_10
Patent number
US08871980B2

Reaction notes

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