Benzeneacetic acid, a-[(phenylmethoxy)methyl]-3-(2-propenyloxy)-, (S)-

Base Information

• Chemical Name: Benzeneacetic acid, a-[(phenylmethoxy)methyl]-3-(2-propenyloxy)-, (S)-
• CAS No.: 155499-21-1
• Molecular Formula: C19H20O4
• Molecular Weight: 312.365
• Mol file: 155499-21-1.mol

Synonyms:

Chemical Property of Benzeneacetic acid, a-[(phenylmethoxy)methyl]-3-(2-propenyloxy)-, (S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzeneacetic acid, a-[(phenylmethoxy)methyl]-3-(2-propenyloxy)-, (S)-

There total 16 articles about Benzeneacetic acid, a-[(phenylmethoxy)methyl]-3-(2-propenyloxy)-, (S)- 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: 91.0%

(R)-2-<3-(allyloxy)phenyl>-3-(benzyloxy)propan-1-ol (155499-19-7) → (S)-2-<3-(allyloxy)phenyl>-3-(benzyloxy)propanoic acid (155499-21-1)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In acetone; at 0 ℃; for 1.5h;

DOI:10.1016/0040-4020(96)00804-6

Reference yield:

ethyl 3-hydroxyphenylacetate (22446-38-4) → (S)-2-<3-(allyloxy)phenyl>-3-(benzyloxy)propanoic acid (155499-21-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / K₂CO₃ / 4 h / 55 °C

2: 90 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

3: 63 percent / DIBALH / CH₂Cl₂ / 0 °C / to room temperature

4: 3A molecular sieves / PPL / 24 h / 0 °C

5: p-TSA / CH₂Cl₂ / Ambient temperature

6: KOH / methanol / Ambient temperature

7: 98 percent / NaH / dimethylformamide / Ambient temperature

8: 93 percent / p-TSA / methanol / Ambient temperature

9: 90 percent / Jones reagent / acetone / 0 °C

With potassium hydroxide; jones reagent; 3 A molecular sieve; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; lithium diisopropyl amide; PPL; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)61382-5

Reference yield:

m-hydroxyphenylacetic acid (621-37-4) → (S)-2-<3-(allyloxy)phenyl>-3-(benzyloxy)propanoic acid (155499-21-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 94 percent / H₂SO₄ / Heating

2: 96 percent / K₂CO₃ / 4 h / 55 °C

3: 90 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

4: 63 percent / DIBALH / CH₂Cl₂ / 0 °C / to room temperature

5: 3A molecular sieves / PPL / 24 h / 0 °C

6: p-TSA / CH₂Cl₂ / Ambient temperature

7: KOH / methanol / Ambient temperature

8: 98 percent / NaH / dimethylformamide / Ambient temperature

9: 93 percent / p-TSA / methanol / Ambient temperature

10: 90 percent / Jones reagent / acetone / 0 °C

With potassium hydroxide; jones reagent; 3 A molecular sieve; sulfuric acid; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; lithium diisopropyl amide; PPL; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)61382-5

upstream raw materials:

(R)-2-<3-(allyloxy)phenyl>-3-(benzyloxy)propan-1-ol

(R)-3-acetoxy-2-<(3-allyloxy)phenyl>propan-1-ol

(S)-2-<3-(allyloxy)phenyl>-3-<(tetrahydropyran-2-yl)oxy>propan-1-ol

(R)-1-acetoxy-2-<3-(allyloxy)phenyl>-3-<(tetrahydropyran-2-yl)oxy>propane

Downstream raw materials:

(S)-ethyl 5-benzyloxy-4-<3-(hydroxy)phenyl>-3-oxopentanoate

(S)-ethyl 4-<3-(allyloxy)phenyl>-5-benzyloxy-3-oxopentanoate

(S)-ethyl 5-benzyloxy-3,3-ethylendithio-4-<3-(hydroxy)phenyl>pentanoate

{2-[(R)-2-Benzyloxy-1-(3-hydroxy-phenyl)-ethyl]-[1,3]dithiolan-2-yl}-acetic acid ethyl ester