Water → Salicylaldehyde

HRID 1659971Notes

Reaction equation

HRID 1659971 reaction equation
[OH-].[Na+].O.[OH:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][OH:8]>[Pd].C(Cl)Cl>[OH:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 962WaterHCID 5146Salicyl AlcoholHCID 14798Sodium Hydroxide

Product 1

HCID 6998Salicylaldehyde

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

In substantially the same manner as in Example 1, 0.16 part of sodium hydroxide, 60 parts of water, 3.2 parts of 5 percent palladium-on-charcoal, 264 parts of methylene chloride and 5 parts of o-hydroxybenzyl alcohol are stirred in the presence of air and refluxed at 45° C.-48° C. for approximately three hours; VPC analysis of the reaction mixture at 160° C. reveals aldehyde formation. The crude reaction mixture is filtered and separated as in Example 1. 2.01 Parts of o-hydroxybenzaldehyde are isolated; 1.49 parts of unreacted o-hydroxybenzyl alcohol are also recovered indicating the reaction had not gone to completion.

Workup

  1. temperaturerefluxed at 45° C.-48° C. for approximately three hours
  2. customat 160° C.
  3. customThe crude reaction mixture
  4. filtrationis filtered
  5. customseparated as in Example 1

Sources & evidence

ORD record
ord-82dc22f6d4954e3f986967d5ae9b8e39
Source dataset
uspto-grants-1981_12
Patent number
US04306083

Reaction notes

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