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Toluene → 2-[4-(Hydroxymethyl)phenyl]benzonitrile

HRID 1047656
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인쇄 미리보기

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HRID 1047656 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.C1(C)C=CC=CC=1.C([O-])(=[O:26])C.[K+].[OH-].[Na+]>O>[OH:26][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1140Toluene2회HCID 14798Sodium HydroxideHCID 517044Potassium AcetateHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

생성물 1

HCID 13938962-[4-(Hydroxymethyl)phenyl]benzonitrile

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
90 °C

실험 절차

A 750 ml flask is charged with 54.4 g (0.2 mol) of 4′-bromomethyl-biphenyl-2-carbonitrile and 250 ml of toluene. To this suspension is added a solution of 30 g (0.3 mol) of potassium acetate in 15 ml of water. The heterogeneous mixture is heated up to an internal temperature of 90° C. to become a clear biphasic solution. After 12 hours at an internal temperature of 90° C. the conversion to the OAc derivative is complete. The biphasic mixture is cooled down to internal temperature of about 50° C. followed by addition of 150 ml NaOH (2N). The mixture is heated up to an internal temperature of ca. 70° C. (extern. temp. 80° C.). After 5 hours at this temperature the PTC saponification is complete (100% conversion, HPLC). Additional 150 ml toluene is added and the warm reaction solution (ca. 50° C.) is washed three times with 50 ml of hot water until the pH is around 7. The toluene phase is evaporated under reduced pressure and the resulting crystalline residue is dried at 50° C. over 24 hours in vacuum to give the white crystalline product with 98% purity (HPLC) and a water content of 0.23%.

후처리

  1. temperatureThe biphasic mixture is cooled down to internal temperature of about 50° C.
  2. temperatureThe mixture is heated up to an internal temperature of ca. 70° C. (extern. temp. 80° C.)
  3. customthe warm reaction solution (ca. 50° C.)
  4. washis washed three times with 50 ml of hot water until the pH is around 7
  5. customThe toluene phase is evaporated under reduced pressure
  6. customthe resulting crystalline residue is dried at 50° C. over 24 hours in vacuum
  7. customto give the white crystalline product with 98% purity (HPLC)

출처 및 근거

ORD 기록
ord-d398485ff99e4dd791d5776049fa8c45
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08569528B2

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