2-Iodoxybenzoic acid → Benzil

HRID 1721529Notes

Reaction equation

HRID 1721529 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]([OH:16])[C@@H:8]([OH:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O>CS(C)=O.O>[C:4]1([C:7]([C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:15])=[O:16])[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 853018Hydrobenzoin, meso-

Product 1

HCID 8651BenzilYield 93%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

meso-Hydrobenzoin (mg 250, 1.17 mmol) was added to a solution of o-iodoxybenzoic acid I (820 mg, 2.93 mmol) in DMSO (15 ml). After 2 hours the solution was diluted with water, filtered and extracted with diethyl ether (3×15 ml). The combined organic layers were washed with water (2×5 ml), dried over sodium sulfate and evaporated to dryness under vacuum. The residue was triturated with n-hexane to give 228 mg (93%) of benzil, mp 91°-94° C. (lit. 94°-95° C.)

Workup

  1. filtrationfiltered
  2. extractionextracted with diethyl ether (3×15 ml)
  3. washThe combined organic layers were washed with water (2×5 ml)
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness under vacuum
  6. customThe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-108c9b0558d94abeb7ab8cf07670e2d9
Source dataset
uspto-grants-1996_04
Patent number
US05510538

Reaction notes

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