2,3-Dimethylphenol → 2-Phenoxybenzoic acid

HRID 1803464Notes

Reaction equation

HRID 1803464 reaction equation
COCCOCCN(CCOCCOC)CCOCCOC.Br[C:24]1[C:25](I)=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([OH:29])=[O:28].C[C:35]1[C:40](C)=[CH:39][CH:38]=[CH:37][C:36]=1[OH:42]>Cl[Cu]>[O:42]([C:25]1[CH:24]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([OH:29])=[O:28])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:35]=1

Participants

5

Reactant 3

HCID 106872,3-DimethylphenolHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 112326623-BROMO-2-IODOBENZOIC ACID

Product 1

HCID 752372-Phenoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

As shown in the Scheme, at the presence of 10% by mole of CuCl and 10% by mole of tris(2-(2-methoxyethoxy)ethyl) amine (TDA-1), 3-bromo-2-iodo benzoic acid was contacted with 2,3-dimethylphenol to yield phenoxybenzoic acid. Without purification, the phenoxybenzoic acid was directly dehydrated and cyclized by reagents such as sulfuric acid, methanesulfonic acid, polyphosphoric acid, or polyphosphate to yield dimethylxanthone. Diethyl malonate was arylated by the dimethylxanthone under catalysis of palladium to yield 5,6-dimethylxanthone-4-ethyl acetate which was hydrolyzed to yield DMXAA.

Sources & evidence

ORD record
ord-1f8b6ca031394897a4c4a145ec3cbca5
Source dataset
uspto-grants-2013_01
Patent number
US08350065B2

Reaction notes

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