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

HRID 1160269

반응식

HRID 1160269 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 acid수율 77.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A 1L 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).

후처리

  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

출처 및 근거

ORD 기록
ord-8ea5cea0fab04f41b2ec230158506c04
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816367B2

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