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

HRID 2426126ノート

反応式

HRID 2426126 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a83cca2808f54cb987d886436135e624
出典データセット
uspto-grants-2011_06
特許番号
US07968554B2

反応ノート

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