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

HRID 1993017ノート

反応式

HRID 1993017 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収率 77.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A 1 L RB flask was charged with compound 1.2 (37 g), diethyl ketone (160 mL), and water (80 mL). The suspension was heated to reflux for 48 h. 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 ethyl acetate:hexanes (1:2). After collecting and drying, the product was obtained as an off-white powder (20.3 g, 77%). 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). MS ESI (pos.) m/e: 205.1 (M+H); 227.1 (M+Na).

後処理

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 48 h
  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 ethyl acetate:hexanes (1:2)
  9. customAfter collecting
  10. customdrying

出典と根拠

ORDレコード
ord-a5b9845883ef4f078b7cd95f0ab6d9a8
出典データセット
uspto-grants-2010_01
特許番号
US07649110B2

反応ノート

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