Ozone → HCID 54077346, compound

HRID 1417761Notes

Reaction equation

HRID 1417761 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])[CH:2]=C.[O:14]=[O+][O-]>C(Cl)Cl>[O:14]=[CH:2][CH2:1][O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 24823OzoneHCID 64838843-Allyloxy-benzoic acid

Product 1

HCID 54077346HCID 54077346, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 300 mg (1.68 mmol) of 3-(2-propenyloxy)benzoic acid in 5 mL of methylene chloride is cooled to -78° C. Ozone is introduced by bubbling the gas into the solution through a glass tube until a blue color persists. The solution is then purged with a stream of argon and 1 mL of methyl sulfide is added. The solution is diluted with 20 mL of ether and washed with water. The organic layer is separated and allowed to stand over magnesium sulfate then concentrated in vacuo to give 283 mg (93%) of 3-(2-oxoethoxy)benzoic acid as a colorless oil. The product is utilized in the next reaction without further purification: m.p. 120°-130°; the 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (KBr) 3400, 3000, 1680, 1590 cm-1 ; MS (CI low res) m/e 181 (M+H), 163, 139, 119.

Workup

  1. customby bubbling the gas into the solution through a glass tube until a blue color persists
  2. customThe solution is then purged with a stream of argon and 1 mL of methyl sulfide
  3. additionis added
  4. additionThe solution is diluted with 20 mL of ether
  5. washwashed with water
  6. customThe organic layer is separated
  7. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-af5bdeea55754aa6bfeffade1e978fc8
Source dataset
uspto-grants-1999_03
Patent number
US05877296

Reaction notes

Loading…