Hydroxyphenylacetic acid → 3-(3,5-Dimethoxyphenyl)-2-(4-hydroxyphenyl)-acrylic acid

HRID 2213349

反応式

HRID 2213349 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:6]=O.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][CH:15]=1.C(OC(=O)C)(=O)C.Cl>C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([OH:13])=[CH:15][CH:16]=2)[C:21]([OH:23])=[O:22])[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1

参加物

6

反応物 4

HCID 127Hydroxyphenylacetic acidHCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 817473,5-Dimethoxybenzaldehyde

生成物 1

HCID 3567513-(3,5-Dimethoxyphenyl)-2-(4-hydroxyphenyl)-acrylic acid

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

反応条件

温度
135 °C

実験手順

To a mixture of 3,5-dimethoxybenzaldehyde (500 g, 3 mol) and p-hydroxyphenyl acetic acid (457 g, 3 mol) was added acetic anhydride (1 L) and triethylamine (420 mL). This non-homogeneous mixture on heating becomes homogeneous at −70° C. After being stirred at 130-140° C. for 6 h, the mixture was cooled to room temperature. Concentrated HCl (1 L) was added to the reaction mixture slowly in 50 min keeping temp between 20-30° C. The light yellow precipitate obtained was filtered and rinsed with Dl water in the Buchner funnel. The solid was dissolved in 3N NaOH (5 L ) and stirred for 1 h and filtered. The filtrate was acidified, maintaining a temperature at 25-30° C., with conc. HCl to pH 1. The precipitated product was filtered and washed with water to give crude product. The crude product was recrystallized from MeOH—H2O then dried at 40° C. for 6 h. Yield: pale yellow solid 428 g (47%). 1HNMR(DMSO-d6): δ 12.48(br, 1H), 9.42(s, 1H), 7.59(s, 1H), 6.95(d, J=8.0 Hz, 2H), 6.76(d, J=8.0 Hz, 2H), 6.35(t, J=2.2 Hz, 1H), 6.27(d,J=2.2 Hz, 2H), 3.56(s, 6H).

後処理

  1. temperatureThis non-homogeneous mixture on heating
  2. custombecomes homogeneous at −70° C
  3. temperaturethe mixture was cooled to room temperature
  4. custombetween 20-30° C
  5. customThe light yellow precipitate obtained
  6. filtrationwas filtered
  7. washrinsed with Dl water in the Buchner funnel
  8. dissolutionThe solid was dissolved in 3N NaOH (5 L )
  9. stirringstirred for 1 h
  10. filtrationfiltered
  11. temperaturemaintaining a temperature at 25-30° C.
  12. filtrationThe precipitated product was filtered
  13. washwashed with water
  14. customto give crude product
  15. customThe crude product was recrystallized from MeOH—H2O
  16. customthen dried at 40° C. for 6 h

出典と根拠

ORDレコード
ord-213ec1c701414bc6adf2f2d4c47f8c5e
出典データセット
uspto-grants-2006_09
特許番号
US07105552B2

関連ノート

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