ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

4-Hydroxybenzaldehyde → 4-(6-Acetoxyhexyloxy)benzaldehyde

HRID 1440952
ノート
印刷プレビュー

反応式

HRID 1440952 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1(S(C)(=O)=O)[CH:14]=[CH:13][C:12]([CH:15]=CC2C=CC=CC=2)=[CH:11][CH2:10]1.[OH:27][C:28]1C=CC(C=O)=C[CH:29]=1.ClCCCCCC[OH:43].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].C(OC(=O)C)(=O)C>O.CC(=O)CC>[C:28]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[O:43])=[CH:13][CH:14]=1)(=[O:27])[CH3:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 6

HCID 1264-HydroxybenzaldehydeHCID 5238Sodium IodideHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 748286-Chloro-1-hexanolHCID 677490264-(6-Hydroxyhexyloxy)-4-methylsulfonylstilbene

生成物 1

HCID 22420484
4-(6-Acetoxyhexyloxy)benzaldehyde

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

An absorption spectrum was taken using the procedures described in Example 1 of the monomeric dipole 4-(6-hydroxyhexyloxy)-4-methylsulfonylstilbene, which has the structural formula: ##STR63## and was prepared as follows: First, 4-(6-acetoxyhexyloxy)benzaldehyde was prepared as follows: A mixture of 81.0 g (0.66 mol) of 4-hydroxybenzaldehyde, 99.7 g (0.73 mol) of 6-chloro-1-hexanol, 70.3 g (0.66 mol) of sodium carbonate, 49.7 g (0.33 mol) of sodium iodide, and 250 mL of 2-butanone was stirred mechanically and heated at reflux for 72 hours. The cooled reaction mixture was filtered, and the solvent was removed at reduced pressure to deposit the 4-(6-hydroxyhexyloxy)benzaldehyde as a brown oil. This oil was dissolved in 200 mL of pyridine, and 74.3 g (0.73 mol) of acetic anhydride was added dropwise with stirring. After the addition was completed, the reaction mixture was heated at reflux for 6 hours, and then cooled to room temperature. The mixture was poured onto 500 mL of water, and the product was extracted into dichloromethane (3 times using 250 mL each time). The combined organic extracts were washed successively with 5% aqueous HCl (2 times using 250 mL each time), and with saturated aqueous NaCl (250 mL). The organic layer was dried over MgSO4, was filtered, and the solvent was removed. The tan oily residue was fractionally distilled at reduced pressure, collecting the product 4-(6-acetoxyhexyloxy)-benzaldehyde at 190°-224° C. and pressure of 0.04 mm. The yield was 84.2 g, which is 48% of theoretical. Proton NMR was performed as in the Examples. 1H NMR (CDCl3) δ: 1.4 (m, 4H), 1.6 (m, 2H), 1.75 (m, 2H), 2.00 (s, 3H), 4.0 (m, 4H), 6.92 (d, 2H), 7.78 (d, 2H), 9.80 (s, 1H).

後処理

  1. custom##STR63## and was prepared
  2. temperatureheated
  3. temperatureat reflux for 72 hours
  4. customThe cooled reaction mixture
  5. filtrationwas filtered
  6. customthe solvent was removed at reduced pressure
  7. dissolutionThis oil was dissolved in 200 mL of pyridine
  8. stirringwith stirring
  9. additionAfter the addition
  10. temperaturethe reaction mixture was heated
  11. temperatureat reflux for 6 hours
  12. extractionthe product was extracted into dichloromethane (3 times using 250 mL each time)
  13. washThe combined organic extracts were washed successively with 5% aqueous HCl (2 times using 250 mL each time)
  14. dry with materialThe organic layer was dried over MgSO4
  15. filtrationwas filtered
  16. customthe solvent was removed
  17. distillationThe tan oily residue was fractionally distilled at reduced pressure
  18. customcollecting the product 4-(6-acetoxyhexyloxy)-benzaldehyde at 190°-224° C.

出典と根拠

ORDレコード
ord-881147d10f734bce9e65fcd9ab119835
出典データセット
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05501821

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート