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100836-85-9

100836-85-9 Structure

100836-85-9 Structure
IdentificationBack Directory
[Name]

(R)-(+)-2-BENZYLOXYPROPIONIC ACID
[CAS]

100836-85-9
[Synonyms]

O-BENZYL-D-LACTIC ACID
(R)-(+)-O-Benzyllactic acid
(R)-2-(Benzyloxy)propanoic acid
(2R)-2-(Benzyloxy)propionic acid
(2R)-2-(benzyloxy)propanoic acid
(R)-(+)-2-BENZYLOXYPROPIONIC ACID
Propanoic acid, 2-(phenylMethoxy)-, (2R)-
(R)-(+)-2-(Benzyloxy)propionic acid[>=97.0% (HPLC)]
[EINECS(EC#)]

628-833-0
[Molecular Formula]

C10H12O3
[MDL Number]

MFCD06799065
[MOL File]

100836-85-9.mol
[Molecular Weight]

180.2
Chemical PropertiesBack Directory
[Melting point ]

52-55 °C
[Boiling point ]

328.2±17.0 °C(Predicted)
[density ]

1.150
[storage temp. ]

Sealed in dry,Room Temperature
[pka]

3.57±0.10(Predicted)
[Appearance]

Off-white to yellow <43°C Solid,>43°C Liquid
[Water Solubility ]

Insoluble in water.
[BRN ]

4675524
[InChI]

InChI=1S/C10H12O3/c1-8(10(11)12)13-7-9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,11,12)/t8-/m1/s1
[InChIKey]

XWAVPOFYNPXXEL-MRVPVSSYSA-N
[SMILES]

C(O)(=O)[C@H](OCC1=CC=CC=C1)C
[CAS DataBase Reference]

100836-85-9
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38-43
[Safety Statements ]

26-36/37
[WGK Germany ]

3
Hazard InformationBack Directory
[Uses]

(R)-(+)-2-Benzyloxypropionic acid is used as a pharmaceutical intermediate.
[Synthesis]

Methyl (R)-2-(Benzyloxy)propionate

115458-99-6

(R)-(+)-2-BENZYLOXYPROPIONIC ACID

100836-85-9

The general procedure for the synthesis of (R)-2-(benzyloxy)propionic acid from methyl (R)-2-(benzyloxy)propionate was as follows: potassium hydroxide (KOH, 9.2 g, 163.96 mmol, 3.00 eq.) was added to methyl (2R)-2-(benzyloxy)propionate (11 g, 56.63 mmol, 1.00 eq.) in a methanol/water (90 mL/10 mL) solution. The reaction mixture was stirred at room temperature for 30 minutes. Upon completion of the reaction, the reaction mixture was concentrated and subsequently diluted with water. The resulting aqueous solution was washed with ethyl acetate and the pH of the aqueous layer was adjusted with aqueous hydrochloric acid to 5. The acidified aqueous layer was extracted with ethyl acetate, the organic layers were combined and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuum to give 9.6 g (94% yield) of (2R)-2-(benzyloxy)propionic acid as a colorless oil.LC-MS detection showed [M + H]+ = 179.

[References]

[1] Patent: WO2015/138934, 2015, A1. Location in patent: Paragraph 00174
[2] Tetrahedron Letters, 1998, vol. 39, # 8, p. 779 - 782
[3] Chemistry - A European Journal, 2015, vol. 21, # 26, p. 9370 - 9379
[4] Angewandte Chemie - International Edition, 2015, vol. 54, # 16, p. 4919 - 4922
[5] Angew. Chem., 2015, vol. 127, # 16, p. 5001 - 5004,4
Spectrum DetailBack Directory
[Spectrum Detail]

(R)-(+)-2-BENZYLOXYPROPIONIC ACID(100836-85-9)1HNMR
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