4-Hydroxybenzoic Acid → Benzoic acid, 4-((1-oxodecyl)oxy)-

HRID 1398092

반응식

HRID 1398092 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[C:13](Cl)(=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl>O.C(O)(C)C>[C:13]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)(=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

참가 물질

7

반응물 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric Acid2회HCID 14798Sodium Hydroxide2회HCID 66982Decanoyl chloride

생성물 1

HCID 3608562Benzoic acid, 4-((1-oxodecyl)oxy)-

시약·촉매·용매 2

HCID 962Water용매HCID 3776Isopropanol용매

반응 조건

온도
67.5 °C

실험 절차

69.1 g (0.5 mol) of para-hydroxybenzoic acid were first dissolved in 200 ml of water and 300 ml of isopropanol and this solution was adjusted to a pH of 10.5 at 20 to 25° C. using 87.4 g of NaOH solution (32% strength by weight aqueous solution, 0.7 mol). Metered in to this solution at a pH of 10.5 subsequently, over the course of three hours, were 95.4 g (0.5 mol) of decanoyl chloride. The pH was held at 10.5 using 40.5 g of NaOH solution (32% strength by weight aqueous solution, 0.324 mol) and the temperature was held at 20 to 25° C. The batch was stirred for one hour thereafter. Subsequently the reaction mixture was adjusted to a pH of 7 at 20 to 25° C. using 5.3 g of HCl solution (32% strength by weight aqueous solution), and the complete solution was heated to 65 to 70° C. and then adjusted to a pH of 1.5 to 3 using 60 g of HCl solution (32% strength by weight aqueous solution). The reaction mixture was cooled to room temperature (25° C.), and the solid was filtered off on a suction filter and washed ten times with 150 ml of water. The yield after drying under reduced pressure at 100° C. was 134.1 g (91.7% of theory). According to HPLC and NMR measurement, the product was free from decanoic acid and from unreacted para-hydroxybenzoic acid. The purity of the product is >99.9% by weight.

후처리

  1. customwas adjusted to a pH of 10.5 at 20 to 25° C.
  2. customover the course of three hours
  3. customwas held at 20 to 25° C
  4. customwas adjusted to a pH of 7 at 20 to 25° C.
  5. temperatureThe reaction mixture was cooled to room temperature (25° C.)
  6. filtrationthe solid was filtered off on a suction
  7. filtrationfilter
  8. washwashed ten times with 150 ml of water
  9. customThe yield
  10. customafter drying under reduced pressure at 100° C.

출처 및 근거

ORD 기록
ord-3d9ff215a2334a9dac5f1d220ee7e2b9
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901342B2

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