Propofol → 2-(Chloromethoxy)-1,3-diisopropylbenzene

HRID 493056

반응식

HRID 493056 반응식
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[OH:13])([CH3:3])[CH3:2].[OH-].[Na+].Br[CH2:17][Cl:18]>C1COCC1>[Cl:18][CH2:17][O:13][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=[CH:7][C:6]=1[CH:10]([CH3:12])[CH3:11]

참가 물질

5

반응물 3

HCID 4943Propofol2회HCID 6333BromochloromethaneHCID 14798Sodium Hydroxide

생성물 1

HCID 112531472-(Chloromethoxy)-1,3-diisopropylbenzene수율 85%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
62.5 °C

실험 절차

A four-necked 500 mL round bottom flask was equipped with a mechanical stirrer, nitrogen inlet, condenser and thermometer. It was charged with 8.9 grams (0.05 moles) of 2,6-diisopropylphenol, 100 mL of THF and 4.0 grams (0.10 mole) of sodium hydroxide pellets. The resultant green suspension was heated to 60-65° C. and held for one hour. The reaction mixture was cooled to 30° C. and 100 mL (199 grams, 1.54 moles) bromochloromethane was added and heating was resumed. The reaction mixture was held at 64° C. for 2-3 hours until no more 2,6-diisopropylphenol was present as measured by GC. After cooling to 25° C., the suspension was filtered through Celite and the filter cake was washed with THF. The THF was removed by rotary evaporation and the resultant oil was distilled under vacuum (0-1 torr, b.p.=80° C.) to give 9.6 grams (0.042 moles, 85% yield) of O-chloromethyl 2,6-diisopropyl phenol.

후처리

  1. customA four-necked 500 mL round bottom flask was equipped with a mechanical stirrer, nitrogen inlet, condenser
  2. temperatureThe reaction mixture was cooled to 30° C.
  3. temperatureheating
  4. temperatureAfter cooling to 25° C.
  5. filtrationthe suspension was filtered through Celite
  6. washthe filter cake was washed with THF
  7. customThe THF was removed by rotary evaporation
  8. distillationthe resultant oil was distilled under vacuum (0-1 torr, b.p.=80° C.)

출처 및 근거

ORD 기록
ord-ed1747f7d3224f5bab4c6d1bf2f236a6
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534776B2

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