Benzyl Chloride → Dibenzyloxybenzaldehyde

HRID 2291656Notes

Reaction equation

HRID 2291656 reaction equation
[OH:1][C:2]1[C:9](O)=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:19](=[O:22])([O-])[O-].[K+].[K+]>C(O)C>[CH2:11]([O:1][C:2]1[C:9]([O:22][CH2:19][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:3]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 905792,3-Dihydroxybenzaldehyde

Product 1

HCID 10870855Dibenzyloxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

13.8 g of 2,3-dihydroxybenzaldehyde, 30.4 g of benzyl chloride and 17.3 g of powdered anhydrous potassium carbonate in 160 ml of anhydrous ethanol are boiled under reflux with exclusion of moisture for 6 hours. The reaction solution is filtered, washing with ethanol, and the filtrate is evaporated in vacuo. On digestion of the residue with diisopropyl ether the known desired compound crystallizes and as white needles (M.p. 89°-91° C.).

Workup

  1. temperatureunder reflux with exclusion of moisture for 6 hours
  2. filtrationThe reaction solution is filtered
  3. washwashing with ethanol
  4. customthe filtrate is evaporated in vacuo
  5. customOn digestion of the residue with diisopropyl ether the known desired compound crystallizes and as white needles (M.p. 89°-91° C.)

Sources & evidence

ORD record
ord-551534122ec6446d96eac137c4d0f25c
Source dataset
uspto-grants-1989_01
Patent number
US04797471

Reaction notes

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