Ethanol → 3-Benzyloxy-4-methoxybenzaldehyde

HRID 2268864Notes

Reaction equation

HRID 2268864 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].C(O)C.C([O-])([O-])=O.[K+].[K+].[CH2:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>[Na+].[I-].O>[CH2:21]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 12127Isovanillin

Product 1

HCID 806713-Benzyloxy-4-methoxybenzaldehydeYield 99.9%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-hydroxy-4-methoxy-benzaldehyde (100 g, 0.657 mole), ethanol (300 ml), K2CO3 (108.9 g, 0.788 mole), benzyl chloride (86.8 ml, 0.755 mole) and NaI (5 g) under N2 was refluxed under stirring for 2.5 hours, then cooled and added with water (900 ml). The precipitate was filtered, washed with water, and then with petrolatum, then dried under vacuum at 40° C. to give 159 g of the title compound which was used as such in the subsequent step.

Workup

  1. temperaturewas refluxed
  2. temperaturecooled
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. dry with materialwith petrolatum, then dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-3be60121798943559f8b2978eba3b142
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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