Acetone → HCID 805695, compound

HRID 703369Notes

Reaction equation

HRID 703369 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. Recrystallizaton from methanol gave the above named product, as a tan flasky solid, in a yield of 51 g (87 percent of theoretical). The product melted at 102°-109° C.; 1H NMR (CDCl3): δ 2.29 (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. customRecrystallizaton from methanol gave the

Sources & evidence

ORD record
ord-a1006c27afeb4a0e9cd2ce9eefc488b2
Source dataset
uspto-grants-1991_01
Patent number
US04983211

Reaction notes

Loading…