4-Hydroxybenzyl Alcohol → 4-Acetoxybenzyl alcohol

HRID 39256

반응식

HRID 39256 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18]>C(OCC)(=O)C>[C:17]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1)(=[O:19])[CH3:18]

참가 물질

5

반응물 3

HCID 1254-Hydroxybenzyl AlcoholHCID 6367Acetyl chlorideHCID 8471Triethylamine

생성물 1

HCID 959064-Acetoxybenzyl alcohol수율 29%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매3회

실험 절차

To a solution of 4-hydroxybenzyl alcohol (7.5 g, 60 mmol) and 8.4 mL of triethylamine (8.4 mL, 60 mmol) in 100 mL of ethyl acetate, cooled in an ice bath, was added, via canula over 15 min, a solution of acetyl chloride (4.7 mL, 66 mmol) in 50 mL of ethyl acetate. The mixture was stirred in the same bath, which was left to come to room temperature on its own. After 18 h, the precipitate was removed by filtration. It was rinsed with 50 mL of ethyl acetate in small portions. The combined filtrates were concentrated in vacuo and purified by flash chromatography on silica gel, using 3:2 hexanes:ethyl acetate as the eluent, to afford 60 (2.853 g, 17 mmol, 29%) as an oil. 1H NMR (400 MHz, CDCl3) δ 2.31 (s, 3H), 4.69 (d, J=5.8 Hz, 2H), 7.08 (d, J=8.6 Hz, 2H), 7.38 (d, J=8.4 Hz, 2H).

후처리

  1. additionwas added, via canula over 15 min
  2. waitwas left
  3. customto come to room temperature on its
  4. customthe precipitate was removed by filtration
  5. washIt was rinsed with 50 mL of ethyl acetate in small portions
  6. concentrationThe combined filtrates were concentrated in vacuo
  7. custompurified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-0b23a32192a74823a75b3149f61fe6ce
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524691B2

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