Benzyl Chloride → 2-Chloro-3-benzyloxy-4-methoxybenzaldehyde

HRID 652802Notes

Reaction equation

HRID 652802 reaction equation
[Cl:1][C:2]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[Cl:1][C:2]1[C:9]([O:10][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

7

Reactant 4

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 603956ChloroisovanilineHCID 5360545Sodium

Product 1

HCID 117478332-Chloro-3-benzyloxy-4-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 78 g of 2-chloro-3-hydroxy-4-methoxybenzaldehyde, 60.7 g of benzyl chloride, 3.9 g of sodium jodide, 74.6 g of potassium carbonate in 0.5 l of 95% ethanol was refluxed for 2 hours. After cooling the mixture was poured in water, the separated product was filtered and then recrystallized from absolute ethanol. 2-chloro-3-benzyloxy-4-methoxybenzaldehyde was obtained, m.p. 86°-88° C.

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationthe separated product was filtered
  3. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-ba149259e75c4324a9cf07c799f34f61
Source dataset
uspto-grants-1987_06
Patent number
US04673671

Reaction notes

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