Hydroxyphenylacetic acid → p-Tetradecyloxyphenylacetic acid

HRID 235688

반응식

HRID 235688 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[OH-].[Na+]>[Cl-].C(C(CCCCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCCCC)N)CCCCCCCCCCCCCCCCC.O>[CH2:25]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

참가 물질

6

반응물 3

HCID 127Hydroxyphenylacetic acidHCID 8208Myristyl bromideHCID 14798Sodium Hydroxide

생성물 1

HCID 10472964p-Tetradecyloxyphenylacetic acid수율 38.4%

시약·촉매·용매 2

HCID 131715051Trioctadecyl methylamine chloride촉매HCID 962Water용매

실험 절차

A mixture of about 75 g of 4-hydroxyphenylacetic acid, about 273.38 g of 1-tetradecylbromide, about 46.33 g of sodium hydroxide, about 5.0 g of trioctadecyl methylamine chloride and about 500 ml of water was refluxed for about 24 hours with stirring, cooled to room temperature, the aqueous layer decanted and the solid washed with water. The solid was refluxed for about 2 hours with stirring in about 500 ml of ethanol containing about 40 g of sodium hydroxide and about 40 ml of water. The solvents were removed and the residue heated at about 0.1 mm and about 200°-210° C. in a Kugelrohr. The residue was stirred with dilute hydrochloric acid and ethyl acetate on a steam bath until solution was complete. The warm solution was washed with brine, then the solvent was removed and the residue recrystallized sequentially from methanol and hexane, giving about 66 g of the desired title compound as a white solid, mp 86°-87° C.

후처리

  1. temperaturewas refluxed for about 24 hours
  2. customthe aqueous layer decanted
  3. washthe solid washed with water
  4. temperatureThe solid was refluxed for about 2 hours
  5. stirringwith stirring in about 500 ml of ethanol containing about 40 g of sodium hydroxide and about 40 ml of water
  6. customThe solvents were removed
  7. temperaturethe residue heated at about 0.1 mm and about 200°-210° C. in a Kugelrohr
  8. stirringThe residue was stirred with dilute hydrochloric acid and ethyl acetate on a steam bath until solution
  9. washThe warm solution was washed with brine
  10. customthe solvent was removed
  11. customthe residue recrystallized sequentially from methanol and hexane

출처 및 근거

ORD 기록
ord-da2ad265cd6e4817bd16622f17529c16
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04640913

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