Benzyl Bromide → 2-(benzyloxy)-4-methoxybenzenecarbaldehyde

HRID 540411Notes

Reaction equation

HRID 540411 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:15][C:16]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:17]=1[CH:18]=[O:19]>CC(C)=O>[CH2:1]([O:15][C:16]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:17]=1[CH:18]=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 696002-Hydroxy-4-Methoxybenzaldehyde

Product 1

HCID 8205272-(benzyloxy)-4-methoxybenzenecarbaldehydeYield 873.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

160 ml (1.3 mmol) of benzyl bromide and (1.3 mmol) of potassium carbonate are added to a solution of 2 g (1.3 mmol) of 2-hydroxy-4-methoxybenzaldehyde in 20 ml of acetone. The mixture is stirred at reflux for 6 hours and then evaporated. 50 ml of 1N aqueous solution of sodium hydroxide are added and the medium is extracted with dichloromethane. The organic phase is dried over magnesium sulphate, filtered and evaporated. The residue obtained is precipitated from 1 heptane/ethyl acetate mixture (95/5). 2.75 g of 2-benzyloxy-4-methoxybenzaldehyde are obtained in the form of a white powder with a yield of 86%.

Workup

  1. temperatureat reflux for 6 hours
  2. customevaporated
  3. addition50 ml of 1N aqueous solution of sodium hydroxide are added
  4. extractionthe medium is extracted with dichloromethane
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue obtained
  9. customis precipitated from 1 heptane/ethyl acetate mixture (95/5)

Sources & evidence

ORD record
ord-a57a77ccfb394b30a727cbe64df1e339
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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