4-Hydroxybenzoic Acid → 4-(7-Octenyloxy)benzoic acid

HRID 1509791

반응식

HRID 1509791 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>O>[CH2:19]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=[CH2:12]

참가 물질

6

반응물 4

HCID 1354-Hydroxybenzoic AcidHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 759078-Bromooct-1-ene

생성물 1

HCID 139976794-(7-Octenyloxy)benzoic acid

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

p-hydroxybenzoic acid (33.2 g), 8-bromo-1-octene (57.3 g), potassium carbonate (41.5 g) and N,N-dimethylacetamide (200 mL) were put into a 500-mL three-neck flask, and stirred at 120° C. for 5 hours. After cooled, the reaction mixture was poured into water (200 mL), extracted with ethyl acetate (500 mL), and washed two times with water (100 mL). This was dried with anhydrous magnesium sulfate and then filtered. The solvent was removed through concentration under reduced pressure, the residue was dissolved in methanol (100 mL), and a methanol solution (20 mL) of potassium hydroxide (16.8 g) was dropwise and gradually added thereto, and heated under reflux for 2 hours. After cooled, the formed crystal was collected through filtration and washed with water. This was dried to give TP-5C (63.3 g, 85%).

후처리

  1. temperatureAfter cooled
  2. extractionextracted with ethyl acetate (500 mL)
  3. washwashed two times with water (100 mL)
  4. dry with materialThis was dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed through concentration under reduced pressure
  7. dissolutionthe residue was dissolved in methanol (100 mL)
  8. additiongradually added
  9. temperatureheated
  10. temperatureunder reflux for 2 hours
  11. temperatureAfter cooled
  12. filtrationthe formed crystal was collected through filtration
  13. washwashed with water
  14. customThis was dried
  15. customto give TP-5C (63.3 g, 85%)

출처 및 근거

ORD 기록
ord-9f45caefc9094fa28cf0559b401885ee
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211598B2

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