Homophthalic acid → 3-(4-Methoxybenzyl)isocoumarin

HRID 432667

Reaction equation

HRID 432667 reaction equation
[C:1]([OH:13])(=O)[CH2:2][C:3]1[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:5]([OH:7])=O.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]C(Cl)=O)=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:1]2[O:13][C:5]([C:4]3[C:3]([CH:2]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[O:7])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 66643Homophthalic acidHCID 27346884-Methoxyphenylacetyl chloride

Product 1

HCID 187602473-(4-Methoxybenzyl)isocoumarinYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
200 °C

Procedure

A well-stirred mixture of homophthalic acid (10 g; 56 mmol) and 2-(4-methoxyphenyl)acetyl chloride (10 g, 230 mmol) was heated at 200° C. for 3 hours under nitrogen then cooled to 50° C. and dissolved in toluene (100 ml), The solvent was removed in vacuo and the residue was dissolved in methanol (100 ml). Silica (30 g) was added and the solvent was removed in vacuo. The crude product, thereby adsorbed onto silica, was applied to the top of a column of silica and purified by chromatography using 10-50% mixtures of ethyl acetate and hexane as eluant. Appropriate fractions were combined and the solvents removed in vacuo to give 3-(4-methoxybenzyl)isocoumarin (0.9 g, 26%) as an oil; δH 3.75 (3H, s), 3.80 (2H, s), 6.50 (1H, s), 6.95 (2H, d, J=8.9 Hz), 7.30 (2H, d, J=8.9 Hz), 7.40-7.90 (3H, m), 8.10 (1H, d); m/z (M+H)+. 267.

Workup

  1. temperaturethen cooled to 50° C.
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in methanol (100 ml)
  4. additionSilica (30 g) was added
  5. customthe solvent was removed in vacuo
  6. custompurified by chromatography
  7. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-63120e174dd04a94ac4274466862b099
Source dataset
uspto-grants-2003_12
Patent number
US06664269B2

Linked notes

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