Acetic Acid → 4-Methoxybenzaldehyde

HRID 649621Notes

Reaction equation

HRID 649621 reaction equation
CC1C=CC(OC)=CC=1.C(O)(=O)C.O.[Na+].[Br-].[C:17](O)(=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1>[Ti]>[CH:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 74784-Methoxybenzoic AcidHCID 77314-MethylanisoleHCID 253881Sodium Bromide

Product 1

HCID 312444-Methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 23963TitaniumCatalyst

Conditions

Temperature
250 fahrenheit

Procedure

Two hundred and thirty (230) g. (1.89 moles) p-methylanisole, 399 g. (6.65 moles) acetic acid, 21 g. (1.17 moles) water, 1.73 g. (0.007 moles) Co(OAc)2 0, 1.7 g. (0.007 moles) Mn(OAc)2.4H2 0 and 1.4 g. (0.014 moles) NaBr were combined in a two-liter titanium-clad autoclave. The reactor was heated to 250° F. and pressurized to 150 psi. The air rate was ramped up to reach a value of 0.78 scf/min after 15 minutes. During the oxidation the temperature and pressure were gradually increased to reach final values of 324° F. and 250 psi. The oxidation was complete after 30 minutes. Analysis of the reaction mixture showed p-anisic acid, 85 mole % yield, and p-anisaldehyde, 1.2 mole % yield.

Workup

  1. customafter 15 minutes
  2. temperatureDuring the oxidation the temperature and pressure were gradually increased
  3. customvalues of 324° F. and 250 psi
  4. customyield

Sources & evidence

ORD record
ord-6517ce408c164a618be0f3ed6d900681
Source dataset
uspto-grants-1988_04
Patent number
US04740614

Reaction notes

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