4-Hydroxybenzaldehyde → 4-[2-(4-Formylphenoxy)ethyl]phenyl acetate

HRID 1595513Notes

Reaction equation

HRID 1595513 reaction equation
CS(O[C:6]1[CH:11]=[CH:10][C:9]([O:15][C:16]([CH3:18])=[O:17])(OCC)[CH2:8][CH:7]=1)(=O)=O.[OH:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1.[OH-].[K+].[C:30](#N)[CH3:31]>>[C:16]([O:15][C:9]1[CH:8]=[CH:7][C:6]([CH2:30][CH2:31][O:19][C:20]2[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=2)=[CH:11][CH:10]=1)(=[O:17])[CH3:18]

Participants

5

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6342AcetonitrileHCID 14797Potassium HydroxideHCID 867573764-(Methylcarbonyloxy)phenetyl methanesulfonate

Product 1

HCID 217049564-[2-(4-Formylphenoxy)ethyl]phenyl acetateYield 95%

Procedure

10.3 g (39.9 mmole) 4-(methylcarbonyloxy)phenetyl methanesulfonate, 5.37 g (44 mmole) p-hydroxybenzaldehyde and 10 g (72.5 mmole) potassium hydroxide were refluxed in 100 ml acetonitrile for 2 hours. The salts were filtered off and the solvents was evaporated. The residue was dissolved in ethyl acetate and washed with water 3 times, dried and evaporated in vacuo to give 10.8 g (yield 95%) of 4-[2-(4-formylphenoxy)ethyl]phenyl acetate.

Workup

  1. filtrationThe salts were filtered off
  2. customthe solvents was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water 3 times
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-1eded6cbb92140309f10375c4fb9dc01
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

Loading…