Hydrochloric Acid → HCID 19801146、化合物

HRID 1646546ノート

反応式

HRID 1646546 の反応式
[CH2:1]([CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Cl:13])[C:5]1=O)[CH:2]=[CH2:3].C1(C)C=CC=CC=1.Cl.O>[Zn].C(O)(=O)C>[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]=[CH2:3]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1140TolueneHCID 22173017HCID 22173017、化合物

生成物 1

HCID 19801146HCID 19801146、化合物収率 64.4%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

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).

後処理

  1. temperatureUpon cooling conventional work-up
  2. customgave a crude product which
  3. customwas purified by chromatography (silica/hexane)

出典と根拠

ORDレコード
ord-6c7aee83fe4e4f9b82d044eddf78b770
出典データセット
uspto-grants-1993_01
特許番号
US05180737

反応ノート

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