Sodium Chloride → 3-(4-Hydroxyphenyl)hex-4-ynoic acid

HRID 731167ノート

反応式

HRID 731167 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]2C(=O)OC(C)(C)[O:14][C:13]2=[O:21])[C:9]#[C:10][CH3:11])=[CH:4][CH:3]=1.C(C(CC)=O)C.[Na+].[Cl-]>O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9]#[C:10][CH3:11])[CH2:12][C:13]([OH:21])=[O:14])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 5234Sodium ChlorideHCID 7288Ethyl ketoneHCID 598551335-(1-(4-Hydroxyphenyl)but-2-yn-1-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

生成物 1

HCID 598551363-(4-Hydroxyphenyl)hex-4-ynoic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A 1 L round-bottom flask was charged with compound M1.2 (37 g), diethyl ketone (160 mL), and water (80 mL). The suspension was heated at reflux for 48 hours. After cooling, the aqueous layer was saturated with NaCl(s) and separated. The organic layer was dried over MgSO4, filtered, and concentrated to a light brown oil, which was crystallized from hot EtOAc:hexanes (1:2). After collecting and drying, the product was obtained as an off-white powder. MS ESI (pos.) m/e: 205.1 (M+H); 227.1 (M+Na). 1H NMR (500 MHz) (DMSO-d6) δ 12.2 (s, 1H); 9.27 (s, 1H); 7.12 (d, 2H, J=8.5 Hz); 6.67 (d, 2H, J=8.6 Hz); 3.87 (m, 1H); 2.54 (m, 2H); 1.82 (d, 3H, J=2.4 Hz).

後処理

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 48 hours
  3. temperatureAfter cooling
  4. customseparated
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to a light brown oil, which
  8. customwas crystallized from hot EtOAc:hexanes (1:2)
  9. customAfter collecting
  10. customdrying
  11. customthe product was obtained as an off-white powder

出典と根拠

ORDレコード
ord-cb083ede4fca4cf4a514613115b0434d
出典データセット
uspto-grants-2009_09
特許番号
US07582803B2

反応ノート

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