4-BENZYLOXY-5-METHOXY-2-NITRO-BENZOIC ACID synthesis
- Product Name:4-BENZYLOXY-5-METHOXY-2-NITRO-BENZOIC ACID
- CAS Number:60547-92-4
- Molecular formula:C15H13NO6
- Molecular Weight:303.27
2426-84-8
60547-92-4
General procedure for the synthesis of 2-nitro-4-benzyloxy-5-methoxybenzoic acid from 4-(benzyloxy)-5-methoxy-2-nitrobenzaldehyde: 4-(benzyloxy)-5-methoxy-2-nitrobenzaldehyde (20 g, 69.62 mmol) was dissolved in acetone (200 mL), and preheated 10% potassium permanganate solution was added slowly at 30 °C. The reaction mixture was stirred at 50 °C for 2 h and then cooled to room temperature. Subsequently, the mixture was filtered through a diatomaceous earth pad and the filter cake was washed with acetone and a little hot water. The filtrate was concentrated under reduced pressure and cooled to 0°C. The concentrate was acidified to pH 4 with hydrochloric acid, stirred for 30 min and filtered to give a solid product of 2-nitro-4-benzyloxy-5-methoxybenzoic acid (18.5 g, 88% yield). The product was confirmed by NMR hydrogen spectrum (300 MHz, DMSO-d6): δ 13.58 (brs, 1H), 7.70 (s, 1H), 7.46-7.40 (m, 6H), 7.39 (s, 1H), 5.25 (s, 2H), 3.92 (s, 3H). Mass spectrum (ESI+, m/z): 304 [M+H]+.
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Yield:60547-92-4 83%
Reaction Conditions:
with sodium hydroxide in ethanol at 65; for 8 h;
Steps:
8 Example 8: 4-(benzyloxy)-3-methoxybenzoic acid
In a mixed solution of 4-hydroxy-3-methoxybenzoic acid (50.0 g, 297.5 mmol) in ethanol (350 mL) and a NaOH solution (2.0 M, 350 mL),BnBr (140.0 g, 823.5 mmol) was added.The mixture is stirred at 65 ° C. for 8 hours, concentrated, co-evaporated to about 400 mL with water (2 x 400 mL), acidified to pH 3.0 with 6M HCl and the solid filtered.Crystallized with EtOH and dried under vacuum at 45 ° C. to give the title compound (63.6 g, 83% yield).
References:
HANGZHOU DAC BIOTECH CO.,LTD. JP2021/73185, 2021, A Location in patent:Paragraph 0203-0204
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