(1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid

Base Information

• Chemical Name: (1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid
• CAS No.: 66823-04-9
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.214
• Mol file: 66823-04-9.mol

Synonyms:(1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid

Chemical Property of (1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 145oC
• Boiling Point: 382.099oC at 760 mmHg
• Flash Point: 199.06°C
• PSA: 57.53000
• Density: 1.310
• LogP: 1.02120

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid

There total 6 articles about (1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 15.0%

(S)-epichlorohydrin (67843-74-7,24969-06-0,13403-37-7) + phenylacetonitrile (140-29-4) → (1S,2S)-2-(hydroxymethyl)-1-phenylcyclopropane-1-carboxylic acid (22613-99-6,66823-04-9,70209-83-5,96847-50-6,96847-51-7) + (1R,2S)-2-oxo-1-phenyl-3-oxabicyclo[3.1.0]hexane (96847-52-8)

Guidance literature:

phenylacetonitrile; With sodium amide; In benzene; at 0 - 20 ℃; for 3h; Inert atmosphere;

(S)-epichlorohydrin; In benzene; at 0 - 20 ℃; for 2h; Further stages; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b01584

Reference yield: 5.2%

(R)-(-)-epichlorohydrin (51594-55-9,24969-06-0,13403-37-7) + phenylacetonitrile (140-29-4) → (1S,2S)-2-(hydroxymethyl)-1-phenylcyclopropane-1-carboxylic acid (22613-99-6,66823-04-9,70209-83-5,96847-50-6,96847-51-7)

Guidance literature:

(R)-(-)-epichlorohydrin; phenylacetonitrile; With sodium amide; In toluene; at 0 - 5 ℃;

With water; potassium hydroxide; In toluene; Reflux;

Reference yield:

(1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one (63106-93-4,96847-52-8,96847-75-5,96847-53-9) → cis-2-Hydroxymethyl-1-phenyl-cyclopropan-1-carbonsaeure (22613-99-6,66823-04-9,70209-83-5,96847-50-6,96847-51-7)

Guidance literature:

With potassium hydroxide; In ethanol; water; at 20 ℃;

DOI:10.1021/jm3011405

upstream raw materials:

(1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one

phenylacetonitrile

(S)-epichlorohydrin

(R)-(-)-epichlorohydrin