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119736-16-2

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Basic Information
CAS No.: 119736-16-2
Name: 3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid
Molecular Structure:
Molecular Structure of 119736-16-2 (3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid)
Formula: C13H10O5
Molecular Weight: 246.219
Synonyms: 2-carboxy-3-benzyloxy-pyran-4(1H)-one;4-Oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic Acid;3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid;2-carboxy-3-benzyloxypyran-4(1H)-one;3-Benzyloxy-4-oxo-4H-pyran-2-carboxylic acid;3-(benzyloxy)-4-oxopyran-2-carboxylic acid;3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylicacid;BPCA;
Density: 1.39±0.1 g/cm3(Predicted)
Boiling Point: 487.5±45.0 °C(Predicted)
PSA: 76.74000
LogP: 1.91700
Related products
Synthetic route
500371-01-7

3-(benzyloxy)-4-oxo-4H-pyran-2-carbaldehyde

119736-16-2

4-oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic acid

Conditions
ConditionsYield
With sodium hypochlorite; aminosulfonic acid In water; acetone at 20℃; for 2h;97%
With sodium chlorite; aminosulfonic acid In water; acetone at 20℃; Cooling with ice;88%
With sodium chlorite; aminosulfonic acid In water; acetone at 20℃; Cooling;86%
119736-15-1

2-(hydroxymethyl)-3-(phenylmethoxy)-4H-pyran-4-one

119736-16-2

4-oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic acid

Conditions
ConditionsYield
With palladium on activated charcoal; oxygen; sodium hydroxide In water at 60℃; under 7600.51 Torr; Autoclave; Green chemistry;92%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide In dichloromethane; water at 5℃; for 1h; Solvent; Reagent/catalyst; Temperature; Large scale;83%
With jones reagent19%

C16H17NO3

119736-16-2

4-oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic acid

Conditions
ConditionsYield
With sodium periodate In water83.5%
Stage #1: C16H17NO3 With sodium periodate; water In N,N-dimethyl-formamide at 25℃; for 0.5h;
Stage #2: With sodium chlorite; aminosulfonic acid; water In N,N-dimethyl-formamide; acetone at 25℃; for 1h;		82%
Multi-step reaction with 2 steps
1: sodium periodate / water; acetone / 5.27 h / 20 °C / Inert atmosphere; Cooling with ice
2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium hypochlorite / water; acetonitrile / 2.63 h / 20 °C / Inert atmosphere; Cooling with ice
View Scheme
61049-69-2

3-O-benzylmaltol

119736-16-2

4-oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic acid

Conditions
ConditionsYield
With chromium(VI) oxide; periodic acid In acetonitrile at 20℃; for 1.5h;71%
Multi-step reaction with 2 steps
1: SeO2 / various solvent(s) / 155 °C
2: NaClO2; NH2SO3H / acetone; H2O
View Scheme
Multi-step reaction with 2 steps
1: SeO2 / various solvent(s) / 12 h / 160 °C
2: NaClO2; aq. H2O2; NaH2PO4 / acetonitrile / 1 h / 20 °C
View Scheme
1229006-11-4

C20H16O3

119736-16-2

4-oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: C20H16O3 With sodium periodate; sulfuric acid; rhodium(III) chloride hydrate In water; acetonitrile at 20℃; for 3.5h;
Stage #2: With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate In ethyl acetate at 25℃; for 1.5h; Product distribution / selectivity;		70%
Stage #1: C20H16O3 With sodium periodate; rhodium(III) chloride hydrate; sulfuric acid In water; acetonitrile at 20℃; for 3.5h;
Stage #2: With sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate In water; acetonitrile at 25℃; for 1.5h; Reagent/catalyst;		70%
Stage #1: C20H16O3 With ruthenium trichloride; sodium periodate
Stage #2: With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical		70%
1206102-05-7

2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one

119736-16-2

4-oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one With sodium periodate; rhodium(III) chloride hydrate; water In ethyl acetate; acetonitrile at 25℃; for 1h;
Stage #2: With sodium chlorite In ethyl acetate; acetonitrile at 25℃; for 1h;		56%
Stage #1: 2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one With sodium periodate; rhodium(III) chloride hydrate In water; ethyl acetate; acetonitrile at 25℃; for 1h;
Stage #2: With sodium chlorite In water; ethyl acetate; acetonitrile at 25℃; for 1h;		56%
Stage #1: 2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one With ruthenium trichloride; sodium periodate In water; ethyl acetate; acetonitrile at 15℃; for 2h; Inert atmosphere;
Stage #2: With sodium chlorite In water; ethyl acetate; acetonitrile at 20℃; for 2h;		52%
Multi-step reaction with 2 steps
1: ruthenium trichloride; sodium periodate; sulfuric acid / acetonitrile; water / 20 °C / Large scale
2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium hypochlorite / acetonitrile; water; ethyl acetate / 20 °C / Large scale
View Scheme
118-71-8

Maltol

119736-16-2

4-oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 83 percent / aq. NaOH / methanol / 75 °C
2: SeO2 / various solvent(s) / 155 °C
3: NaClO2; NH2SO3H / acetone; H2O
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / methanol / 8 h / Reflux
2: selenium(IV) oxide / 14 h / 159 °C
3: sodium hypochlorite; aminosulfonic acid / water; acetone / 2 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetonitrile / Inert atmosphere; Reflux; Large scale
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -60 °C / Inert atmosphere
2.2: 2 h / -60 °C / Inert atmosphere
3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 2 h / -30 °C / Inert atmosphere
3.2: 0.33 h / 0 °C
4.1: ruthenium trichloride; sodium periodate / acetonitrile; ethyl acetate; water / 2 h / 15 °C / Inert atmosphere
4.2: 2 h / 20 °C
View Scheme
100-39-0

benzyl bromide

ZnCr-benzoate*3H2O

ZnCr-benzoate*3H2O

119736-16-2

4-oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 83 percent / aq. NaOH / methanol / 75 °C
2: SeO2 / various solvent(s) / 155 °C
3: NaClO2; NH2SO3H / acetone; H2O
View Scheme
100-44-7

benzyl chloride

119736-16-2

4-oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / methanol / 8 h / Reflux
2: selenium(IV) oxide / 14 h / 159 °C
3: sodium hypochlorite; aminosulfonic acid / water; acetone / 2 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
2: aminosulfonic acid; sodium hypochlorite
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / methanol / 1 h / Reflux
2: periodic acid; chromium(VI) oxide / acetonitrile / 1.5 h / 20 °C
View Scheme
100-39-0

benzyl bromide

119736-16-2

4-oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetonitrile / Inert atmosphere; Reflux; Large scale
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -60 °C / Inert atmosphere
2.2: 2 h / -60 °C / Inert atmosphere
3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 2 h / -30 °C / Inert atmosphere
3.2: 0.33 h / 0 °C
4.1: ruthenium trichloride; sodium periodate / acetonitrile; ethyl acetate; water / 2 h / 15 °C / Inert atmosphere
4.2: 2 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetonitrile / 5 h / 80 °C
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -60 °C
2.2: 1 h / -60 °C
3.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 30 °C
3.2: 0.5 h / 30 °C
4.1: sodium periodate; rhodium(III) chloride hydrate; water / acetonitrile; ethyl acetate / 1 h / 25 °C
4.2: 1 h / 25 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / acetonitrile / 5 h / 13 - 80 °C / Large scale
2: bromobenzene; selenium(IV) oxide / 13 h / 140 °C / Dean-Stark
3: sodium chlorite; aminosulfonic acid / water; acetone / 0.67 h / 20 °C / Cooling with ice
View Scheme
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    119736-16-2

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    Product Name: 3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid Synonyms: 3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid;4-oxo-3-((phenylmethyl)oxy)-4h-pyran-2-carboxylic acid;4-Oxo-3-(phenylmethoxy)-4H-pyran-2-carboxylic acid;4-oxo-3-phenylmethox

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