ChemicalBook CAS DataBase List 4-isobutyloxybenzyl isocyanate

4-isobutyloxybenzyl isocyanate synthesis

11synthesis methods

Product Name:4-isobutyloxybenzyl isocyanate
CAS Number:639863-75-5
Molecular formula:C12H15NO2
Molecular Weight:205.25

2-[4-(2-methylpropoxy)phenyl]acetic acid

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Yield:639863-75-5 94%

Reaction Conditions:

Stage #1: 2-[4-(2-methylpropoxy)phenyl]acetic acidwith N,N,N',N'-tetramethyl-1,8-diaminonaphthalene in tetrahydrofuran at 20; for 0.416667 h;
Stage #2: with diphenyl phosphoryl azide in tetrahydrofuran at -20 - 20; for 26 h;Heating / reflux;

Steps:

1.4

Step 4; 1-Isobutoxy-4-(isocyanatomethyl)benzene: To a solution of 2-(4-Isobutoxyphenyl)acetic acid (1 g, 4.8 mmol) in anhydrous tetrahydrofuran (3 mL) was added N,N,N',N'-tetramethylnaphthalene-1,8-diamine (1.03 g, 4.8 mmol) at ambient temperature under nitrogen atmosphere. After stirring for 25 minutes, diphenylphosphorylazide (1.32 g, 4.8 mmol) was added dropwise and then the mixture was heated to reflux for 6 hours. The reaction mixture was cooled to ambient temperature and then stored at -20° C. for 20 hours to precipitate out ammonium phosphonate salt. A mixture of ether and ethyl acetate (v/v=1/1, 5 mL) was added to the cold reaction mixture. The precipitate formed was filtered off and the cake was washed with ether/ethyl acetate (1/1, v/v, 4 mL). The filtrate was concentrated in vacuo to dryness to afford the title compound (800 mg, 94% yield) which was used directly in next step without further purification.

References:

US2008/280886,2008,A1 Location in patent:Page/Page column 21-22

32315-10-9 Synthesis