ChemicalBook CAS DataBase List METHYL 3-ACETYL-4-HYDROXYBENZOATE

METHYL 3-ACETYL-4-HYDROXYBENZOATE synthesis

9synthesis methods

Product Name:METHYL 3-ACETYL-4-HYDROXYBENZOATE
CAS Number:57009-12-8
Molecular formula:C10H10O4
Molecular Weight:194.18

111-34-2 Synthesis

111-34-2
260 suppliers
$13.00/25mL

29415-97-2 Synthesis

29415-97-2
171 suppliers
$5.00/1g

57009-12-8
56 suppliers
$30.00/100mg

Yield: 82%

Reaction Conditions:

Stage #1:-butyl vinyl ether;methyl 3-bromo-4-hydroxybenzoate with triethylamine;(diphenylphosphin)ferrocene;palladium diacetate in diethyl ether;ethanol at 70;Inert atmosphere;
Stage #2: with hydrogenchloride;water in dichloromethane for 2 h;

Steps:

1.00.2
Step 2 To a degassed solution of methyl 3-bromo-4-hydroxybenzoate (350 g, 1514.87 mmol) in ethanol (3 L) were added triethylamine (0.528 L, 3787.17 mmol), 1-(vinyloxy)butane (0.588 L, 4544.60 mmol), 1,1'-bis(diphenylphosphino)ferrocene (33.1 g, 60.6 mmol) and diacetoxypalladium (8.50 g, 37.9 mmol) under nitrogen. The mixture was heated at 70° C. overnight. The reaction was cooled down, filtered and the filtrate concentrated. The resulting solid was solubilized with DCM (2 L) and HCl 4N (1.14 L, 4544 mmol) was added under stirring. Stirring was maintained for 2 hrs, the organic phase was separated, dried over magnesium sulfate, filtered and concentrated to afford a solid which was stirred in diethyl ether (5 L) for 2 hrs. The solid was filtered off and the filtrate concentrated to dryness to afford methyl 3-acetyl-4-hydroxybenzoate (240 g, 82%) as a beige powder. Mass spectrum: [M-H]^- 193.

References:

ASTRAZENECA AB US2011/98271, 2011, A1 Location in patent:Page/Page column 39

67-56-1 Synthesis