Acetone → Benzaldehyde, 4-(phenylmethoxy)-

HRID 1471340Notes

Reaction equation

HRID 1471340 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)C(C)=NN=1.C(Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:21]([O-:24])([O-])=O.[K+].[K+].CC(C)=[O:29]>>[CH2:21]([O:24][C:8]1[CH:7]=[CH:6][C:11]([CH:2]=[O:29])=[CH:10][CH:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2697331-Chloro-4-methylphthalazine

Product 1

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-Yield 86%

Conditions

Temperature
65 °C

Procedure

A mixture of 4-hydroxybenzaldehyde (1) (3.05 g, 25.00 mmol), benzyl bromide (4.4 g, 25.75 mmol), and K2CO3 (4.25 g, 30.75 mmol) in acetone (75 mL) is stirred at 65° C. under argon for 19.5 h, then cooled to room temperature, and concentrated at reduced pressure to remove the acetone. The residue is diluted with 2 N HCl (60 mL) and extracted with ethyl acetate (80 mL and 50 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is purified on silica gel (16.7% ethyl acetate/hexane) to give 4.56 g (86%) of 2 as a white solid, mp 70-72° C. IR 2943, 1738, 1484, 1230 cm−1; 1H NMR (CDCl3) δ 5.19 (s, 2H, CH2), 7.11 (d, J=8.7 Hz, 2H, 3,5-ArH), 7.36-7.49 (m, 5H, PhH), 7.87 (d, J=8.7 Hz, 2H, 2,6-ArH), 9.92 ppm (s, 1H, CHO).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated at reduced pressure
  3. customto remove the acetone
  4. additionThe residue is diluted with 2 N HCl (60 mL)
  5. extractionextracted with ethyl acetate (80 mL and 50 mL)
  6. washThe extract is washed (brine)
  7. customdried
  8. customAfter solvent removal at reduced pressure
  9. customthe residue is purified on silica gel (16.7% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-50ea461ddb754c279e283d800b4474e0
Source dataset
uspto-grants-2015_04
Patent number
US09012217B2

Reaction notes

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