Water → 4-Methoxybenzaldehyde

HRID 1897553Notes

Reaction equation

HRID 1897553 reaction equation
CCN(CC)CC.[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1.O.C(C1C=C(C(C)(C)C)C=C(C(C)(C)C)C=1)(C)(C)C>ClCCCl>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1

Participants

6

Conditions

Temperature
60 °C

Procedure

Complex 8 (8.8 mg, 0.021 mmol) and NEt3 (14 μL, 0.10 mmol) were dissolved in 1,2-dichloroethane (2 mL). The solution was added to a flask containing 4-methoxybenzyl alcohol (140 mg, 1.01 mmol), H2O (91 μL, 5.05 mmol), and a 1,3,5-tri-tert-butylbenzene internal standard (19.2 mg, 0.078 mmol). The flask was equipped with an air condenser and a stir bar and heated at 60° C. for 24 h with stirring (˜700 rpm). The reaction mixture was cooled to room temperature, the solvent removed under vacuum, and the extent of conversion determined by integration of the 1H NMR spectrum against the internal standard. 4-Methoxybenzaldehyde was formed in >98% yield (based on the average of two runs of this type).

Workup

  1. additionThe solution was added to a flask
  2. customThe flask was equipped with an air condenser and a stir bar
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-382456599fac430aa212b1678c67eb9e
Source dataset
uspto-grants-2013_08
Patent number
US08519132B2

Reaction notes

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