Hydrochloric Acid → HCID 19801146, compound

HRID 1646546Notes

Reaction equation

HRID 1646546 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 19801146HCID 19801146, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-6c7aee83fe4e4f9b82d044eddf78b770
Source dataset
uspto-grants-1993_01
Patent number
US05180737

Reaction notes

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