Acetone → HCID 805695, compound

HRID 1084667Notes

Reaction equation

HRID 1084667 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:19][C:20]([CH3:22])=[O:21]>O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[CH:19][C:20](=[O:21])[CH3:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 78109Benzaldehyde, 4-(phenylmethoxy)-

Product 1

HCID 805695HCID 805695, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 50 g (0.2 mol) of 4-benzyloxybenzaldehyde in 500 mL of acetone was diluted with 500 mL of water. To the cloudy emulsion which formed was added 20 mL of 1N sodium hydroxide and the mixture stirred at room temperature for 20 hours. The solids which precipitated were recovered by filtration. Recrystallization from methanol gave the above named product, as a tan flaky solid, in a yield of 51 g (87 percent of theoretical). The product melted at 102°-109° C.; 1H NMR (CDCl3) δ2.29 (s, 3H, CH3 --), 5.04 (s, 2H, --CH2 --), 6.48-7.52 (m, 11H, ArH's and --CH=CH--).

Workup

  1. customTo the cloudy emulsion which formed
  2. customThe solids which precipitated
  3. filtrationwere recovered by filtration
  4. customRecrystallization from methanol
  5. customgave the

Sources & evidence

ORD record
ord-14aa5c060f27408598430e40f55a6169
Source dataset
uspto-grants-1991_04
Patent number
US05006159

Reaction notes

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