Name | benzyloxyacetic acid |
Synonyms | RARECHEM AL BE 0628 BENZYLOXYACETIC ACID benzyloxyacetic acid benzyloxy acctic acid benzyloxy acctic acid 2-(benzyloxy)acetic acid PHENYLMETHOXY ACETIC ACID ACETIC ACID, (PHENYLMETHOXY)- Acetic acid, 2-(phenylMethoxy)- |
CAS | 30379-55-6 |
InChI | InChI=1/C9H10O3/c10-9(11)7-12-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11) |
Molecular Formula | C9H10O3 |
Molar Mass | 166.17 |
Density | 1.162 g/mL at 25 °C (lit.) |
Melting Point | 80-81 °C |
Boling Point | 137-139 °C/0.6 mmHg (lit.) |
Flash Point | >230°F |
Vapor Presure | 9.33E-05mmHg at 25°C |
Appearance | clear liquid |
Color | Colorless to Light orange to Yellow |
pKa | 3.52±0.10(Predicted) |
Storage Condition | Sealed in dry,Room Temperature |
Refractive Index | n20/D 1.526(lit.) |
Physical and Chemical Properties | benzyloxyacetic acid is a colorless liquid at normal temperature and pressure. Benzyloxyacetic acid is a carboxylic acid derivative, which has a certain degree of acidity and can dissociate Carboxylate ions in water. |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
WGK Germany | 3 |
HS Code | 29189900 |
Hazard Class | IRRITANT |
Use | Benzyloxyacetic acid can be used as an intermediate in pharmaceutical chemistry and organic synthesis. In the synthetic transformation, the carboxyl group in the structure can be easily converted into ester groups or reactive functional groups such as hydroxyl groups. In the reported literature, the most commonly used method is to convert the carboxyl group into acid chloride, the benzyl group can then be connected to the target molecular structure through the conversion of acid chloride. In addition, the benzyl group in the structure can be removed by palladium-carbon hydrogenation under reacidic conditions to obtain the corresponding hydroxy acid product. |
Synthesis method | Cool the reaction bottle to 0 degrees in an ice water bath, and dissolve sodium hydride (60% dispersed in a solution of tetrahydrofuran (100ml) in 10 minutes In mineral oil, 330 mmol) suspension is added to benzyl alcohol (38.8 ml, 375 mmol), pay attention to the reaction will obviously appear bubbles, during operation, the pressure balance in the reaction bottle should be kept as much as possible, and the bubbles should stop coming out. Under the condition of cooling, the solution of bromoacetic acid (150mmol) in tetrahydrofuran (50mL) should be added within 10 minutes. After adding, the ice bath should be removed, the mixed solution should be stirred at ambient temperature for 12 hours, and then the mixed solution of water (150mL) and n-hexane (100mL) should be slowly added into the reaction system, dissolve the reaction system in this biphasic mixture, separate the water layer, acidify the water layer with concentrated hydrochloric acid (12M,40mL), then extract the water layer with diethyl ether (2 × 100 mL), clean the combined organic extract with brine (50 mL), dry the combined organic extract with anhydrous magnesium sulfate, and filter to remove the concentrated organic extract of magnesium sulfate solid to obtain benzyloacetic acid. Figure The synthesis route of benzyloxyacetic acid |