application of methyl 4-hydroxyphenylacetate_kain industrial additive

overview^[1]

methyl 4-hydroxyphenylacetate is an organic intermediate that can be used to synthesize 4-isobutoxybenzylamine. 4-isobutoxybenzylamine is a key intermediate in the synthesis of pimaserin and has broad applications. market prospects.

apply^[1]

methyl 4-hydroxyphenylacetate can be used to synthesize 4-isobutoxybenzylamine.

using 4-hydroxyphenylacetic acid (2) as raw material, esterification reaction produces 4-hydroxyphenylacetic acid methyl ester (3); (3) substitution reaction produces 4-isobutoxyphenylacetic acid methyl ester (4) ), the obtained product (4) is hydrolyzed to obtain 4-isobutoxyphenylacetic acid (5); (5) undergoes acylation reaction to produce 4-isobutoxyphenylacetamide (6); (6) is reacted by hofmann furman) degradation reaction generates n-(4-hydroxybenzyl) methyl carbamate (7); (7) is hydrolyzed to obtain the target product (1).

preparation^[1]

synthesis of methyl 4-hydroxyphenylacetate:

add p-hydroxyphenylacetic acid (5.0g (gram), 32.86mmol (millimol)) into a 100ml (ml) round-bottomed flask, then add 30ml methanol to dissolve it, and add dropwise 2.5ml of 98% concentrated sulfuric acid. , heated to 80°c (celsius) for reflux reaction, and after 0.5h (hour) it was detected by tlc (thin layer chromatography) and the reaction was completed. spin off the methanol under reduced pressure at 50°c, add 100 ml of water, extract with ethyl acetate (50 ml × 3), combine the organic phases, wash with saturated brine (100 ml × 3), and finally dry with anhydrous sodium sulfate, spin dry to obtain yellow color oily substance 4-hydroxyphenylacetic acid methyl ester 3 5.3g, yield 91.58%. ¹h nmr (400mhz, cdcl₃) δ: 7.08 (d, j＝8.3hz, 2h), 6.73 (d, j＝8.3hz, 2h), 3.69 (s,3h),3.55(s,2h);¹³c nmr (100mhz, cdcl₃)δ: 40.30, 51.97, 115.96, 125.40, 130.40, 156.16, 172.52.

main reference materials

[1] [chinese invention] cn201810213656.x a synthesis method of 4-isobutoxybenzylamine