2-(2-(allyloxy)phenyl)acetic acid

Base Information

• Chemical Name: 2-(2-(allyloxy)phenyl)acetic acid
• CAS No.: 99558-25-5
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.214

Synonyms:2-(2-(allyloxy)phenyl)acetic acid

Chemical Property of 2-(2-(allyloxy)phenyl)acetic acid

Chemical Property:

Purity/Quality:

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Technology Process of 2-(2-(allyloxy)phenyl)acetic acid

There total 4 articles about 2-(2-(allyloxy)phenyl)acetic 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: 73.0%

allyl bromide (106-95-6) + 2-Hydroxyphenylacetic acid (614-75-5) → 2-(2-(allyloxy)phenyl)acetic acid (99558-25-5)

Guidance literature:

With potassium hydroxide; In methanol; at 70 ℃; for 2h;

DOI:10.1039/c6cc10178j

Reference yield:

(2-allyloxyphenyl)acetic acid methyl ester (153623-44-0) → 2-(2-(allyloxy)phenyl)acetic acid (99558-25-5)

Guidance literature:

With lithium hydroxide; In methanol; water;

DOI:10.1016/S0040-4039(01)01303-X

Reference yield:

methyl (2-hydroxyphenyl)acetate (22446-37-3) → 2-(2-(allyloxy)phenyl)acetic acid (99558-25-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH; tetra-n-butyl ammonium iodide

2: LiOH / methanol; H₂O

With lithium hydroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; In methanol; water;

DOI:10.1016/S0040-4039(01)01303-X

upstream raw materials:

allyl bromide

2-Hydroxyphenylacetic acid

(2-allyloxyphenyl)acetic acid methyl ester

methyl (2-hydroxyphenyl)acetate

Downstream raw materials:

4-(2-allyloxyphenyl)-4,5-dihydropyridazin-3(2H)-one

(2-Allyloxy-phenyl)-acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl ester

(2-Allyloxy-phenyl)-acetic acid (2S,4aR,6S,7R,8S,8aS)-8-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

(2-Allyloxy-phenyl)-acetic acid (2S,4aR,6R,7R,8S,8aS)-6-((2R,3R,4S,5R,6S)-4-acetoxy-5-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Refernces

The 2-(allyloxy) phenyl acetyl ester as a new relay protecting group for oligosaccharide synthesis

10.1016/S0040-4039(01)01303-X

The research focuses on the development and application of the 2-(allyloxy) phenyl acetyl (APAC) group as a novel protecting group for oligosaccharide synthesis. The APAC group is designed to be orthogonal to levulinoyl and acetyl esters, allowing for selective removal without affecting these sensitive esters. The study demonstrates that APAC can be efficiently removed using a relay deprotection approach involving Pd(PPh3)4 and proton sponge, which cleaves the phenolic allyl ether and enables intramolecular ester cleavage by nucleophilic attack. Experiments involved the synthesis of 2-(allyloxy) phenyl acetic acid and its subsequent use to protect hydroxyl groups in various glycosyl donors. The APAC-protected donors were then used in glycosylation reactions with different acceptors to form disaccharides, with exclusive formation of 1,2-trans glycosides due to neighboring group participation. The orthogonality of APAC with other esters was confirmed through selective deprotection experiments. Analytical techniques such as NMR, MS, and TLC were employed to characterize the compounds and monitor reaction progress.

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