Ozone → 4-Chloro-2,3-dihydro-1H-indene-2-ethanol

HRID 1646547Notes

Reaction equation

HRID 1646547 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])[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

Participants

5

Reactant 2

HCID 24823OzoneHCID 19801146HCID 19801146, compound

Product 1

HCID 543631014-Chloro-2,3-dihydro-1H-indene-2-ethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

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. 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

Sources & evidence

ORD record
ord-a2b0c7514c7e45569e60cd63199b343b
Source dataset
uspto-grants-1993_01
Patent number
US05180737

Reaction notes

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