Benzyl 5-hydroxypent-2-ynoate

Base Information

• Chemical Name: Benzyl 5-hydroxypent-2-ynoate
• CAS No.: 136258-78-1
• Molecular Formula: C₁₂H₁₂O₃
• Molecular Weight: 204.225
• DSSTox Substance ID: DTXSID00567820
• Wikidata: Q82453843
• Mol file: 136258-78-1.mol

Synonyms:BENZYL 5-HYDROXYPENT-2-YNOATE;136258-78-1;2-Pentynoic acid, 5-hydroxy-, phenylmethyl ester;benzyl 5-hydroxy-2-pentynoate;benzyl 5--hydroxy-2-pentynoate;SCHEMBL6642914;DTXSID00567820;FYDQVJJMOBIAKQ-UHFFFAOYSA-N;BENZYL5-HYDROXYPENT-2-YNOATE

Chemical Property of Benzyl 5-hydroxypent-2-ynoate

Chemical Property:

• PSA: 46.53000
• LogP: 1.11560
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 204.078644241
• Heavy Atom Count: 15
• Complexity: 253

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C#CCCO

Technology Process of Benzyl 5-hydroxypent-2-ynoate

There total 1 articles about Benzyl 5-hydroxypent-2-ynoate 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:

3-butynyl ethoxyethyl ether (18669-05-1) + benzyl chloroformate (501-53-1,94274-21-2) → benzyl 5-hydroxy-2-pentynoate (136258-78-1)

Guidance literature:

With hydrogenchloride; n-butyllithium; Yield given. Multistep reaction; 1) -78 deg C, 2) acetone;

DOI:10.1016/0040-4039(91)80689-4

Reference yield:

benzyl 5-hydroxy-2-pentynoate (136258-78-1) → 2-Hydroxymethyl-3-methyl-6-(3-oxo-butyl)-cyclohex-2-enone (136258-89-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) HgO, BF₃*Et₂O / 1) 1 h, 60 deg C, 2a) 0.5 h, 70 deg C, b) 24 h, 20 deg C

2: H₂ / Pd(OH)2 / propan-2-ol / 2625.2 Torr

3: 1) CsHCO₃, 2) 1 N HCl / 1) MeOH, 24 h, 20 deg C, 2) 1 h, 20 deg C

With hydrogenchloride; cesium bicarbonate; boron trifluoride diethyl etherate; hydrogen; mercury(II) oxide; palladium dihydroxide; In isopropyl alcohol;

DOI:10.1016/0040-4039(91)80689-4

Reference yield:

benzyl 5-hydroxy-2-pentynoate (136258-78-1) → 3-(2-Methoxy-4-oxo-5,6-dihydro-4H-pyran-3-yl)-2-phenylselanyl-propionic acid ethyl ester (136258-86-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) HgO, BF₃*Et₂O / 1) 1 h, 60 deg C, 2a) 0.5 h, 70 deg C, b) 24 h, 20 deg C

2: H₂ / Pd(OH)2 / propan-2-ol / 2625.2 Torr

3: CsHCO₃ / methanol; tetrahydrofuran / 24 h / 20 °C

4: diethyl ether / 20 °C

With cesium bicarbonate; boron trifluoride diethyl etherate; hydrogen; mercury(II) oxide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; isopropyl alcohol;

DOI:10.1016/0040-4039(91)80689-4

upstream raw materials:

3-butynyl ethoxyethyl ether

benzyl chloroformate

Downstream raw materials:

4-(benzyloxy)-5,6-dihydro-2H-pyran-2-one

5,6-dihydro-4-methoxy-2H-pyran-2-one

2-Hydroxymethyl-3-methyl-6-(3-oxo-butyl)-cyclohex-2-enone

3-(2-Methoxy-4-oxo-5,6-dihydro-4H-pyran-3-yl)-2-phenylselanyl-propionic acid ethyl ester