Methanol → 3-Methoxyisophthalaldehydic acid methyl ester

HRID 1111758Notes

Reaction equation

HRID 1111758 reaction equation
C[C:2]1[C:3]([O:15][CH3:16])([C:12](O)=[O:13])[CH:4](C)[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[H-].[CH2:18]([Al+]CC(C)C)C(C)C.CO>C1(C)C=CC=CC=1.CCCCCC>[CH3:18][O:8][C:6](=[O:7])[C:5]1[CH2:4][C:3]([O:15][CH3:16])([CH:2]=[CH:10][CH:9]=1)[CH:12]=[O:13]

Participants

6

Reactant 3

HCID 887MethanolHCID 21225700DiisobutylaluminumhydrideHCID 86736056Dimethyl 3-methoxyisophthalic acid

Product 1

HCID 867360553-Methoxyisophthalaldehydic acid methyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

To a -78° C. to -100° C. solution of 1.0 mole of dimethyl 3-methoxyisophthalic acid in 5 liters of toluene is slowly added 1.0 mole of diisobutylaluminum hydride as a 1M solution in n-hexane (reaction t ≤ -78° C.). The reaction mixture is stirred for 3 hours following the addition and is then quenched by the addition of 10 moles of anhydrous methanol. The reaction mixture is allowed to warm to room temperature and is stirred until a filterable precipitate forms. The reaction mixture is filtered and the filtrate evaporated. The residue is purified by vacuum distillation to yield 3-methoxyisophthalaldehydic acid methyl ester.

Workup

  1. customTo a -78° C. to -100° C.
  2. additionthe addition
  3. stirringis stirred until a filterable precipitate forms
  4. filtrationThe reaction mixture is filtered
  5. customthe filtrate evaporated
  6. distillationThe residue is purified by vacuum distillation

Sources & evidence

ORD record
ord-7e28c598cd014eee96c8a4e619016065
Source dataset
uspto-grants-1978_10
Patent number
US04118559

Reaction notes

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