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27475-09-8

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Basic Information
CAS No.: 27475-09-8
Name: 2-BENZYL-5-ACETYL METHYL SALICYLATE
Article Data: 20
Molecular Structure:
Molecular Structure of 27475-09-8 (2-BENZYL-5-ACETYL METHYL SALICYLATE)
Formula: C17H16O4
Molecular Weight: 284.312
Synonyms: 5-acetyl-2-benzyloxybenzoic acid methyl ester;benzyl ether of methyl 5-acetylsalicylate;Methyl 5-Acetyl-2-(Benzyl-Oxy)Benzoate;5-acetyl-2-(phenylmethoxy)benzoic acid,methyl ester;2-Benzyloxy-5-acetylbenzoic Acid Methyl Ester;Y6153;estere metilico dell'acido 5-acetil-2-benzilossibenzoico;
Density: 1.167g/cm3
Boiling Point: 443.482oC at 760 mmHg
Flash Point: 196.816oC
PSA: 52.60000
LogP: 3.25480
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Synthetic route
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estere metilico dell'acido 5-acetilsalicilico

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benzyl bromide

27475-09-8

5-acetyl-2-benzyloxybenzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 85℃; for 9h;100%
With potassium carbonate In acetonitrile at 75℃; for 16h;100%
With potassium carbonate In acetonitrile for 24h;96.6%
100-39-0

benzyl bromide

27475-09-8

5-acetyl-2-benzyloxybenzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: estere metilico dell'acido 5-acetilsalicilico With potassium carbonate In acetonitrile for 0.166667h;
Stage #2: benzyl bromide In methanol at 85℃; for 9.25h;		100%
16475-90-4

estere metilico dell'acido 5-acetilsalicilico

100-44-7

benzyl chloride

27475-09-8

5-acetyl-2-benzyloxybenzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 50 - 65℃; for 2h;98.5%
With sodium carbonate In N,N-dimethyl-formamide at 110 - 115℃; for 2h;84.7%
With sodium In ethanol for 30h; Heating;55%
With sodium carbonate; sodium iodide In acetonitrile for 16h; Heating / reflux;55%
With potassium carbonate
16475-90-4

estere metilico dell'acido 5-acetilsalicilico

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benzyl bromide

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butanone

27475-09-8

5-acetyl-2-benzyloxybenzoic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride; potassium carbonate71.4%
...Expand
27475-09-8

5-acetyl-2-benzyloxybenzoic acid methyl ester

27475-14-5

2-benzyloxy-5-(2-bromoacetyl)benzoic acid methyl ester

Conditions
ConditionsYield
With bromine In chloroform at 0 - 20℃; Inert atmosphere;97%
With N-Bromosuccinimide; sulfuric acid In acetonitrile at 50℃; for 1h;81%
With aluminium trichloride; bromine In diethyl ether for 3h; Ambient temperature;78%
27475-09-8

5-acetyl-2-benzyloxybenzoic acid methyl ester

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5-acetyl-2-(benzyloxy)benzoic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In tetrahydrofuran; methanol91%
Stage #1: 5-acetyl-2-benzyloxybenzoic acid methyl ester With sodium hydroxide; water In tetrahydrofuran; methanol for 8h;
Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water		91%
Stage #1: 5-acetyl-2-benzyloxybenzoic acid methyl ester With sodium hydroxide; water In tetrahydrofuran; methanol for 8h;
Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water		91%
27475-09-8

5-acetyl-2-benzyloxybenzoic acid methyl ester

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N,N-dimethyl-formamide dimethyl acetal

A

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methanol

B

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methyl 2-(benzyloxy)-5-(3-(dimethylamino)acryloyl)benzoate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 110 - 115℃; for 8h;A n/a
B 82.1%
...Expand
27475-09-8

5-acetyl-2-benzyloxybenzoic acid methyl ester

5-(1-amino-ethyl)-2-benzyloxy-benzoic acid methyl ester

Conditions
ConditionsYield
With ammonium acetate; sodium cyanoborohydride In methanol
27475-09-8

5-acetyl-2-benzyloxybenzoic acid methyl ester

2-benzyloxy-5-(1-{2-[3-(4-carbamimidoyl-phenyl)-ureido]-acetylamino}-ethyl)-benzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaCNBH3; NH4OAc / methanol
2: O-[(EtOCO)cyanomethyleneamino]-N,N,N',N'-Me4-uronium*BF4; N-ethylmorpholine / dimethylformamide
View Scheme
27475-09-8

5-acetyl-2-benzyloxybenzoic acid methyl ester

2-Hydroxymethyl-4-(1-hydroxy-2-pyrrolidin-1-yl-ethyl)-phenol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 78 percent / AlCl3, bromine / diethyl ether / 3 h / Ambient temperature
2: 2.) HCl / 1.) 15 h, reflux; 2.) ether, alcohol
3: 44 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating
4: 68 percent / hydrogen / 10percent Pd/C / 760 Torr / Ambient temperature
View Scheme
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