33533-53-8

Usage

Uses

Used in Fragrance Industry:
1-Phenylethyl hydrogen phthalate is used as a fixative for perfumes to prolong the scent and enhance its intensity. It is also used to enhance and blend other fragrance ingredients, making it a valuable component in the creation of various perfumes and scented products.
It is important to use 1-Phenylethyl hydrogen phthalate with caution and in accordance with safety guidelines, as it can be an irritant to the skin, eyes, and respiratory system.

InChI:InChI=1/C16H14O4/c1-11(12-7-3-2-4-8-12)20-16(19)14-10-6-5-9-13(14)15(17)18/h2-11H,1H3,(H,17,18)

Upstream product

• 100-52-7 benzaldehyde 
• 85-44-9 phthalic anhydride 
• 98-85-1 1-Phenylethanol 

Downstream Products

• 98-85-1 1-Phenylethanol 
• 19321-43-8 (R)-α-methylbenzyl hydrogen phthalate 
• 100836-99-5 2-{[(S)-1-phenylethoxy]carbonyl}benzoic acid 
• 1517-69-7 (+)-α-phenethyl alcohol 
• 98-85-1 (-)-α-phenethyl alcohol 
• 585-71-7 (+)-1-phenylbromoethane 

Relevant academic research and scientific papers

Enzyme-mediated enantioselective hydrolysis of soluble polymer-supported carboxylates

The enzyme-mediated enantioselective hydrolysis of water-soluble polymer-supported carboxylates is disclosed. The representative monomethoxy poly(ethylene glycol) (MPEG, av MW 5000)-supported substrate was synthesized by immobilization of (±)-1-phenylethanol onto the modified MPEG (MPEG/NH2) through an carboxylate linker with a succinate spacer. For the screening of the hydrolytic enzymes, the substrate was enantioselectively hydrolyzed by lipase from Candida antarctica (Novozym 435) in a mixed solvent (hexane/buffer=9/1) at 30 °C to afford the remaining (S)-substrate and the resulting (R)-alcohol (E value>200). The products were easily separated by a simple procedure without any laborious column chromatography. The substrate was hydrolyzed with NaOH in MeOH/H2O to afford the corresponding (S)-alcohol. We also found that the structure of the spacer between the MPEG moiety and the carboxylate linker strongly affected both the reactivity and enantioselectivity, and the substrate bearing a glutarate spacer gave the best result. Our procedure was applicable for the preparation of several optically active alcohols.

Use of (S)-α-methylbenzylamine in the resolution of racemic 2-octanol and α-methylbenzyl alcohol

The title chiral amine can be a convenient substitute for brucine or strychnine in Ingersoll's classical method for the resolution of alcohols via fractional crystallization of their diastereoisomeric phthalate salts.

EFFECT OF THE NATURE OF THE ACYLATING AGENT ON THE ASYMMETRIC ACYLATION OF ALCOHOLS

During the acylation of racemic 1-phenylethanol by the action of carboxylic acid anhydrides in the presence of S-(-)-N,N-dimethyl-α-phenylethylamine the unreacted alcohol is enriched in the S isomer.Its optical purity increases with increase in the steric demands of the anhydride from 2percent for acetic anhydride to 9percent for benzoic anhydride.When carboxylic acid chlorides are used, optically active 1-phenyl-1-chloroethane and bis-1-phenylethyl ether are isolated in addition to S-(-)-1-phenylethanol.

Preparation of chiral 1-phenylethanols and bromides

A fast, convenient procedure for preparing and resolving moderate to large quantities of chiral secondary alcohols is described.The general procedure involves a one-pot conversion of the ketone (various acetophenones) to the half-ester of a diacid (succinic, phthalic...) and resolution with (+)- and (-)-1-phenylethylamines.Overall yields of the enantiomeric alcohols, the variously substituted 1-phenylethanols, are generally 65-85percent with optical purities of approximately 90percent.Properties and optical rotations of a number of chiral 1-phenylethanols and of the bromides made from them are tabulated.A discussion of optical purity determinations using nmr methods is included and absolute configurations are reported.