Hydrochloric Acid → 8-phenoxyoctanoic Acid

HRID 611661

반응식

HRID 611661 반응식
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].Cl>CCO.O>[O:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 14798Sodium HydroxideHCID 5482758-Bromooctanoic acid

생성물 1

HCID 102203288-phenoxyoctanoic Acid수율 76%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

Phenol (1.88 g, 20 mmol) was mixed with NaOH (0.80 g, 20 mmol) in EtOH (50 mL). 8-Bromooctanoic acid (2.23 g, 10 mmol) was then added to the mixture and refluxed for 12 h. After cooling to room temperature, water (100 mL) was added and the mixture was acidified with 2N HCl (pH=2). The solid was filtered and washed with water (2×50 mL), and recrystallized from hexane-ethyl acetate (5:1) to give the product as white brick-like crystals (1.79 g, 76%), mp 67-68° C.; 1H-NMR: 1.42 (m, 6 H), 1.65 (m, 2 H), 1.80 (m, 2 H), 2.37 (t, 2 H), 3.97 (t, 2 H), 6.93 (m, 3 H), 7.30 (t, 2 H), 10.05 (bs, 1 H). Anal. Calcd. for C14H20O3 : C, 71.16, H, 8.53%; Found: C, 71.09, H, 8.54%.

후처리

  1. temperaturerefluxed for 12 h
  2. filtrationThe solid was filtered
  3. washwashed with water (2×50 mL)
  4. customrecrystallized from hexane-ethyl acetate (5:1)

출처 및 근거

ORD 기록
ord-06875566834849a3bc55cdedd745eb16
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06001869

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