Phenol → Benzene, (hexadecyloxy)-

HRID 327855

반응식

HRID 327855 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[C:18]1([OH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[K+].C1(C)C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:18]1([O:24][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

7

반응물 4

HCID 996PhenolHCID 1140TolueneHCID 82131-BromohexadecaneHCID 14797Potassium Hydroxide

생성물 1

HCID 4438129Benzene, (hexadecyloxy)-수율 98%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매

반응 조건

온도
92 °C

실험 절차

A 1-liter three necked round bottom flask was charged with 100 grams (0.33 moles) of 1-bromohexadecane, 92.5 grams (0.99 moles) of phenol, 55.2 grams (0.99 moles) of potassium hydroxide, 10 grams of tetra-n-butylammonium bromide, 167 ml of toluene, and 167 ml of water. The flask was fitted with a mechanical stirrer, nitrogen inlet, condenser, thermometer and heating mantle. The reaction mixture was heated to reflux at about 92° C., under a nitrogen purge for 16 hours with constant agitation. After 16 hours, the mixture was cooled and transferred to a separatory funnel where the aqueous layer was removed and the upper toluene layer was washed three times with 200 ml 0.5N NAOH and three times with 200 ml deionized water. The toluene was removed under reduced pressure leaving 102.6 grams (98% yield) of n-hexadecyl phenyl ether. Analysis by gas chromatography showed that the product was 98.3% pure.

후처리

  1. customThe flask was fitted with a mechanical stirrer, nitrogen inlet, condenser
  2. temperaturethermometer and heating mantle
  3. temperatureThe reaction mixture was heated
  4. custompurge for 16 hours with constant agitation
  5. temperaturethe mixture was cooled
  6. customtransferred to a separatory funnel
  7. customwhere the aqueous layer was removed
  8. washthe upper toluene layer was washed three times with 200 ml 0.5N NAOH and three times with 200 ml
  9. customThe toluene was removed under reduced pressure

출처 및 근거

ORD 기록
ord-bf66e1cdae314981bd734c887691cbc3
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05274148

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