Hydrochloric Acid → HCID 19801146, Verbindung

HRID 1646546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1646546
[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]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1140TolueneHCID 22173017HCID 22173017, Verbindung

Produkt 1

HCID 19801146HCID 19801146, VerbindungAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-6c7aee83fe4e4f9b82d044eddf78b770
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05180737

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