Ozone → HCID 89851711, compound

HRID 1771439Notes

Reaction equation

HRID 1771439 reaction equation
[CH2:1]([O:8][CH:9]([CH2:18][CH:19]=C)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:21]=[O+][O-]>C(Cl)Cl>[CH2:1]([O:8][CH:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[CH2:18][CH:19]=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24823OzoneHCID 89852182HCID 89852182, compound

Product 1

HCID 89851711HCID 89851711, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-(benzyloxy)pent-4-enyl)-2-methylbenzene (5.0 g, 18.72 mmol) in DCM (100 ml) was passed O3 gas at −78° C. for 3 h. The reaction mixture was quenched with TEA (5 ml) at −78° C., and stirred for room temperature for 5 h. The title compound was purified by separation methods A and E. (Yield 2.0 g).

Workup

  1. customat −78° C.
  2. customfor 3 h
  3. customThe reaction mixture was quenched with TEA (5 ml) at −78° C.
  4. customThe title compound was purified by separation methods A and E

Sources & evidence

ORD record
ord-30e96a26e322428290daeb347e25332f
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

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