Ozone → Dimethyl 5-(benzyloxy)-4-(2-oxoethyl)isophthalate

HRID 1177365Notes

Reaction equation

HRID 1177365 reaction equation
[CH2:1]([C:4]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[C:22]([O:24][CH3:25])=[O:23])[CH:2]=C.[O:26]=[O+][O-]>C(Cl)Cl.CO>[CH2:15]([O:14][C:13]1[C:4]([CH2:1][CH:2]=[O:26])=[C:5]([C:22]([O:24][CH3:25])=[O:23])[CH:6]=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 24823OzoneHCID 15281704Dimethyl 4-allyl-5-(benzyloxy)isophthalate

Product 1

HCID 59560096Dimethyl 5-(benzyloxy)-4-(2-oxoethyl)isophthalateYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of dimethyl 4-allyl-5-(benzyloxy)isophthalate (3.5 g, 10.28 mmol) in CH2Cl2 and methanol was cooled to −78° C. and treated with ozone until the solution appeared blue (20 min). Nitrogen was bubbled through the solution until the blue color dissipated. Dimethylsulfide (1.0 mL) was added and the cold-bath was removed allowing the reaction mixture to warm to room temperature overnight. Concentration of the solution under vacuum provided an oil which was purified by column chromatography on silica gel eluted with 10-30% EtOAc in hexanes to afford the aldehyde (3.0 g, 98%) as a white solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 3.90 (s, 3 H) 3.95 (s, 3 H) 4.29 (s, 2 H) 5.14 (s, 2 H) 7.31-7.56 (m, 5 H) 7.81 (d, J=1.32 Hz, 1 H) 8.29 (d, J=1.51 Hz, 1 H) 9.75 (s, 1 H); MS (ESI, pos): 343.

Workup

  1. custom(20 min)
  2. customNitrogen was bubbled through the solution until the blue color
  3. additionDimethylsulfide (1.0 mL) was added
  4. customthe cold-bath was removed
  5. customConcentration of the solution under vacuum provided an oil which
  6. customwas purified by column chromatography on silica gel
  7. washeluted with 10-30% EtOAc in hexanes

Sources & evidence

ORD record
ord-1b022e40b8f54fa4b5c0b0b017ffaef3
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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