4-Hydroxybenzyl Alcohol → 1-[4-(Hydroxymethyl)phenoxy]propan-2-one

HRID 1516055ノート

反応式

HRID 1516055 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:17][C:18](=[O:20])[CH3:19]>CC(C)=O>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:17][C:18](=[O:20])[CH3:19])=[CH:3][CH:4]=1

参加物

5

反応物 3

HCID 1254-Hydroxybenzyl AlcoholHCID 6571ChloroacetoneHCID 11430Potassium Carbonate

生成物 1

HCID 177562771-[4-(Hydroxymethyl)phenoxy]propan-2-one収率 98%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a stirred solution of 4-hydroxybenzyl alcohol (1.0 g, 8.06 mmol) in acetone (80 mL) was added potassium carbonate (1.34 g, 9.68 mmol) and chloroacetone (0.771 mL, 9.68 mmol). After completion of addition the reaction mixture was heated to reflux. After 20 hours the reaction mixture was cooled down to room temperature and the solvent was removed. Water and ethyl acetate were added to the crude material. The aqueous layer was separated and extracted with ethyl acetate (3×, 100 mL). All combined organic layers were dried over Na2SO4, filtered, and concentrated to provide an oil. The crude material was purified using silica gel chromatography (gradient from 4:1 to 1:1 pentane:ethyl acetate) to provide the desired product (0.981 g, 5.45 mmol) in 98% yield. 1H (CDCl3, 600 MHz): δ 7.30 (2H, d, J=8.7 Hz), 6.87 (2H, d, J=8.7 Hz), 4.63 (2H, d, J=5.7 Hz), 4.54 (2H, s), 2.27 (3H, s), 1.66 (1H, t, J=5.8 Hz); 13C (CDCl3, 150 MHz): δ 205.7, 157.3, 134.3, 128.8, 114.6, 73.1, 64.8, 26.6.

後処理

  1. additionAfter completion of addition the reaction mixture
  2. temperaturewas heated to reflux
  3. customthe solvent was removed
  4. additionWater and ethyl acetate were added to the crude material
  5. customThe aqueous layer was separated
  6. extractionextracted with ethyl acetate (3×, 100 mL)
  7. dry with materialAll combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto provide an oil
  11. customThe crude material was purified

出典と根拠

ORDレコード
ord-b0d72a6e024643e0af2fc951456e237a
出典データセット
uspto-grants-2012_07
特許番号
US08226929B2

反応ノート

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