Ozone → 2-(4-Chloro-2-indanyl) ethanol

HRID 1646547노트

반응식

HRID 1646547 반응식
[CH2:1]([CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Cl:13])[CH2:5]1)[CH:2]=C.[O:14]=[O+][O-]>CO.ClCCl>[Cl:13][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH2:12][CH:4]([CH2:1][CH2:2][OH:14])[CH2:5]2

참가 물질

5

반응물 2

HCID 24823OzoneHCID 19801146HCID 19801146, 화합물

생성물 1

HCID 543631012-(4-Chloro-2-indanyl) ethanol

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

Amalgamated zinc (prepared from zinc powder (6 g), mercuric chloride (0.6 g)) was heated under reflux for 7 hours with 2-allyl-4-chloro-indan-1-one (3 g), toluene (20 ml), conc. hydrochloric acid (20 ml), water (8 ml) and acetic acid (2 ml). Upon cooling conventional work-up gave a crude product which was purified by chromatography (silica/hexane) to give a 2-allyl-4-chloroindane (1.8 g). 2-Allyl-4-chloroindane (0.8 g) in dry methanol (10 ml) and dry dichloromethane (2 ml) was reacted at -35° with ozone until the blue colour persisted. After purging with nitrogen the solution was stirred 16 hours with dimethyl sulphide (2.58 g). The volatiles were removed and the residue taken up in tetrahydrofuran (10 ml) and heated under reflux with 4-toluenesulphonic acid (30 mg) and water (circa 0.5 ml) for 2 hours. After conventional work up the product, 2-(4-chloro-2-indanyl) ethanol, was obtained as a yellow oil (0.8 g).

후처리

  1. customAfter purging with nitrogen the solution
  2. customThe volatiles were removed
  3. temperatureheated
  4. temperatureunder reflux with 4-toluenesulphonic acid (30 mg) and water (circa 0.5 ml) for 2 hours

출처 및 근거

ORD 기록
ord-a2b0c7514c7e45569e60cd63199b343b
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05180737

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