Hydrochloric Acid → 5-(4-Chloro-benzyloxy)-2-methyl-phenol

HRID 2426126노트

반응식

HRID 2426126 반응식
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[C:10]([OH:16])[CH:9]=2)=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[CH:15]=[CH:14][C:11]([CH3:12])=[C:10]([OH:16])[CH:9]=2)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 5003444Sodium cyanoborohydrideHCID 861018764-(4-Chloro-benzyloxy)-2-hydroxybenzaldehyde

생성물 1

HCID 575815955-(4-Chloro-benzyloxy)-2-methyl-phenol

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-(4-chloro-benzyloxy)-2-hydroxybenzaldehyde (1.31 g, 5.0 mmol) and sodium cyanoborohydride (1.0 g, 15.9 mmol, Aldrich) in tetrahydrofuran (30 mL) was added methyl orange as an indicator, giving the solution a yellow color; 1N aqueous HCl solution (7.5 mL) was added slowly, keeping the solution orange. The mixture was then stirred overnight at room temperature. Water was added, and the mixture was extracted with ethyl acetate three times. The combined organic phase was washed with water and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography eluting with 0-40% ethyl acetate in hexanes to give 5-(4-chloro-benzyloxy)-2-methyl-phenol. (Yield 0.43 g).

후처리

  1. customgiving the solution a yellow color
  2. extractionthe mixture was extracted with ethyl acetate three times
  3. washThe combined organic phase was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 0-40% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-a83cca2808f54cb987d886436135e624
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968554B2

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