Triphenylphosphine → HCID 58479486, compound

HRID 39412Notes

Reaction equation

HRID 39412 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]1[C:12](=C(C)C)[CH:7]2[CH2:6][CH2:5]1.[O:16]=[O+][O-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]1[C:12](=[O:16])[CH:7]2[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 24823Ozone2×HCID 674531575-Chloro-9-isopropylidene-1,2,3,4-tetrahydro-1,4-methano-naphthalene

Product 1

HCID 58479486HCID 58479486, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

In a 20 liter reactor, 600 g of 5-chloro-9-isopropylidene-1,2,3,4-tetrahydro-1,4-methano-naphthalene (27.43 mol) were charged in a mixture of 13 l CH2Cl2 and 0.5 l of MeOH. The reaction mixture was cooled down at −40° C. and an ozone stream (55 kg/h) was feed until change of color. After elimination of the ozone residue, PPh3 (23.83 mol) was added and reaction mixture was heated to ambient temperature. The purification was done via chromatography. 421 g white solid product was isolated with a purity >98%.

Workup

  1. customreaction mixture
  2. temperaturewas heated to ambient temperature
  3. customThe purification

Sources & evidence

ORD record
ord-c8fb69fd08994709bd52e564019ff23e
Source dataset
uspto-grants-2013_09
Patent number
US08524915B2

Reaction notes

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