Ozone → HCID 13066661, compound

HRID 1163984Notes

Reaction equation

HRID 1163984 reaction equation
[O:1]=[O+][O-].[CH:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[C:8]=1[OH:21])=CC>C(OCC)(=O)C.C(O)(=O)C>[OH:21][C:8]1[C:9]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])=[CH:10][CH:11]=[CH:12][C:7]=1[CH:4]=[O:1]

Participants

5

Reactant 2

HCID 24823OzoneHCID 53993459HCID 53993459, compound

Product 1

HCID 13066661HCID 13066661, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ozone gas was introduced into a solution of 2-(1-propenyl)-6-(o-tolyloxy)phenol (13.7 g) in a mixture of ethyl acetate (300 ml) and acetic acid (50 ml) at 0°-3° C. with stirring for an hour. The reaction mixture was washed with water, aqueous sodium bicarbonate and saline successively, dried over magnesium sulfate and when evaporated. The oily residue (12.9 g) was dissolved in diethyl ether, and the solution was washed with water, dried over magnesium sulfate and evaporated. The oily residue (11.7 g) was pulverized and recrystallized from methanol to give 2-hydroxy-3-(o-tolyloxy)benzaldehyde (4.8 g). mp 56°-58° C.

Workup

  1. washThe reaction mixture was washed with water, aqueous sodium bicarbonate and saline successively
  2. dry with materialdried over magnesium sulfate and when
  3. customevaporated
  4. dissolutionThe oily residue (12.9 g) was dissolved in diethyl ether
  5. washthe solution was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-2a2d2bad6dde422da264121a815f6d80
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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