Homophthalic acid → 3-(4-Methoxybenzyl)isocoumarin

HRID 432667

반응식

HRID 432667 반응식
[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

참가 물질

4

반응물 2

HCID 66643Homophthalic acidHCID 27346884-Methoxyphenylacetyl chloride

생성물 1

HCID 187602473-(4-Methoxybenzyl)isocoumarin수율 26%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
200 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-63120e174dd04a94ac4274466862b099
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664269B2

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