Compounds derived from aryloxyacetic acids

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C14H12O3

mol.wt. 228.25

Syntheses

OH

-Preparation by hydrogenolysis of 2-benzyloxyα-phenoxyacetophenone in ethanol/dioxane (1:1) in the presence of Pd/C under hydrogen (85%) [1417]. -Also obtained by acidic hydrolysis of 4-hydroxy3-phenoxycoumarin (m.p. 216°) [810] according to [996]. -Also prepared by reaction of phenoxyacetonitrile with phenol (Hoesch reaction) [1025]. -Also refer to: [160]. COCH 2 O

m.p. 115-115°5 [1417], 115° [810]; UV [1417]. 1-(4-Hydroxyphenyl)-2-phenoxyethanone [41978-29-4]

C14H12O3

mol.wt. 228.25

Synthesis

OH

-Refer to: [1234] [1267] (Japanese papers). m.p. 159-160° [1267]; b.p.2 212-220° [1267]. COCH2 O 1-(2,4-Dihydroxyphenyl)-2-phenoxyethanone [73014-19-4]

C14H12O4

mol.wt. 244.25

Syntheses

OH COCH2O HO

-Obtained by reaction of phenoxyacetonitrile with resorcinol (Hoesch reaction) [78] [1382] [1498] [1499], (88%) [1496], (82%) [1417]. -Also refer to: [540] [567].

m.p. 209°5-210° [1417], 207-208° [1496], 204-205° [1382]; 1H NMR [1496], UV [1417]. 2-Phenoxy-1-(2,4,6-trihydroxyphenyl)ethanone [72023-07-1]

C14H12O5 Syntheses

OH COCH2O HO

mol.wt. 260.25

OH

-Preparation by reaction of phenoxyacetonitrile with phloroglucinol (Hoesch reaction), (84%) [1417], (80%) [541], (48%) [1575]. -Also refer to: [1185] [1545] [1559].

152

HYDROXYACETOPHENONES m.p. 275° (d) [1575], 244-245° [1417], 234° [541]. One note a very large dispersion of the various melting points. 1H NMR [541], UV [1417].

1-(2-Hydroxy-4-methoxyphenyl)-2-phenoxyethanone [73023-08-2]

C15H14O4

mol.wt. 258.27

Syntheses

OH COCH2O CH3O

-Obtained by partial methylation of 2,4-dihydroxyα-phenoxyacetophenone with dimethyl sulfate in the presence of potassium carbonate in boiling acetone for 2.5 h (83%) [1417]. -Also refer to: [1498].

m.p. 86°5-87° [1417]; UV [1417]. 1-(2-Hydroxy-5-methoxyphenyl)-2-phenoxyethanone [137612-24-9]

C15H14O4

mol.wt. 258.27

Syntheses

OH COCH 2 O

OCH3

-Obtained by acylation of hydroquinone monomethyl ether with phenoxyacetonitrile in the presence of boron trichloride and aluminium chloride in ethylene dichloride (44%) [1026]. -Also refer to: [1025].

1-(4-Hydroxy-3-methoxyphenyl)-2-phenoxyethanone [41978-28-3]

C15H14O4

mol.wt. 258.27

Syntheses

OH OCH3

COCH2O

-Obtained (by-product, unusual result) by methylation of 2-(3-chlorophenoxy)-1-(4-hydroxy-3-methoxyphenyl)ethanone [397]. -Also refer to: [1267] (Japanese paper). m.p. 94°5-95° [1267]; b.p.2 218-225° [1267].

1-(5-Ethyl-2,4-dihydroxyphenyl)-2-phenoxyethanone [243465-56-7]

C16H16O4

mol.wt. 272.30

Synthesis

OH COCH2O HO C 2H 5

-Obtained [540] by previously described methods [1185].

COMPOUNDS DERIVED FROM ARYLOXYACETIC ACIDS

153

1-(2-Hydroxy-4,6-dimethoxyphenyl)-2-phenoxyethanone [73023-09-3]

C16H16O5 Synthesis

OH COCH2O

-Obtained by partial methylation of 2,4,6-trihydroxyα-phenoxyacetophenone with dimethyl sulfate in the presence of potassium carbonate in boiling acetone for 8 h (63%) [1417].

OCH3

CH3O

mol.wt. 288.30

m.p. 122-123° [1417]; UV [1417]. 1-[3,5-Bis-(1,1-dimethylethyl)-4-hydroxyphenyl]-2-phenoxyeth