Methanol → 3-Methoxyisophthalaldehydic acid methyl ester

HRID 1105959Notes

Reaction equation

HRID 1105959 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH2:5][C:6]([O:14][CH3:15])([CH:11]=[CH:12][CH:13]=1)[C:7](OC)=[O:8].[H-].C([Al+]CC(C)C)C(C)C.CO>C1(C)C=CC=CC=1.CCCCCC>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH2:5][C:6]([O:14][CH3:15])([CH:11]=[CH:12][CH:13]=1)[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 887MethanolHCID 205314733-Methoxyisophthalic acid dimethyl esterHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 867360553-Methoxyisophthalaldehydic acid methyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

To a -78° to -100° solution of 1.0 mol of 3-methoxyisophthalic acid dimethyl ester in 1-10 l of toluene is slowly added 1.0 mol of diisobutylaluminum hydride as a 1 M solution in n-hexane. The reaction is stirred for 3 hours after the addition and then quenched by the addition of 10 mol of anhydrous methanol. The reaction is allowed to warm to room temperature and stirred until a filterable precipitate forms. The reaction is filtered and the filtrate evaporated to a residue. The residue is purified by crystallization, distillation or chromatography to yield 3-methoxyisophthalaldehydic acid methyl ester.

Workup

  1. customTo a -78° to -100°
  2. additionafter the addition
  3. stirringstirred until a filterable precipitate forms
  4. filtrationThe reaction is filtered
  5. customthe filtrate evaporated to a residue
  6. distillationThe residue is purified by crystallization, distillation or chromatography

Sources & evidence

ORD record
ord-ec766c54defe4057a4a1009c93782fb7
Source dataset
uspto-grants-1982_01
Patent number
US04310668

Reaction notes

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