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

HRID 731167

반응식

HRID 731167 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cb083ede4fca4cf4a514613115b0434d
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582803B2

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