5-(1,1-dimethylethyl)salicylic acid synthesis

9synthesis methods

Product Name:5-(1,1-dimethylethyl)salicylic acid
CAS Number:16094-31-8
Molecular formula:C11H14O3
Molecular Weight:194.23

2725-53-3 Synthesis

2725-53-3
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$20.00/1g

16094-31-8
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$44.00/100mg

Yield: 77.4%

Reaction Conditions:

Stage #1:2-hydroxy-5-t-butylbenzaldehyde with sodium chlorite;sodium dihydrogenphosphate;aminosulfonic acid in 1,4-dioxane;water at 0; for 1 h;
Stage #2: with sodium sulfite in 1,4-dioxane;water for 0.5 h;

Steps:

11.1
Sulfamic acid(1.76g, 18.1mmol) and sodium dihydrogenphosphate(7.33g, 47mmol) were added to a solution of 5-[(1,1-dimethyl)ethyl]-2-hydroxybenzaldehyde(2.15g, 12.1mmol) in 1,4-dioxane(100mL) and water(40mL). A solution of sodium chlorite(1.76g, 15.5mmol) in water(10mL) was added to the mixture under ice cooling, and it was stirred for 1 hour. Then, sodium sulfite(1.80g, 14.3mmol) was added to the mixture, and it was stirred for 30 minutes. Concentrated hydrochloric acid was added to the reaction mixture, and pH was adjusted to 1. The residue obtained by evaporation of 1,4-dioxane under reduced pressure was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was washed with n-hexane under suspension to give the title compound(1.81g, 77.4%) as a white powder.1H-NMR(DMSO-d6):δ 1.26(9H, s), 6.90(1H, d, J=9.0Hz), 7.58(1H, dd, J=8.7, 2.4Hz), 7.75(1H, d, J=2.4Hz), 11.07(1H, brs).

References:

Institute of Medicinal Molecular Design, Inc. EP1535609, 2005, A1 Location in patent:Page/Page column 74