3-((E)-5-Carboxy-3-methyl-pent-2-enyl)-5-chloro-2-hydroxy-4-methoxy-benzoic acid methyl ester

Base Information

Chemical Name:3-((E)-5-Carboxy-3-methyl-pent-2-enyl)-5-chloro-2-hydroxy-4-methoxy-benzoic acid methyl ester
CAS No.:171826-77-0
Molecular Formula:C₁₆H₁₉ClO₆
Molecular Weight:342.776
Hs Code.:

Synonyms:3-((E)-5-Carboxy-3-methyl-pent-2-enyl)-5-chloro-2-hydroxy-4-methoxy-benzoic acid methyl ester

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Chemical Property of 3-((E)-5-Carboxy-3-methyl-pent-2-enyl)-5-chloro-2-hydroxy-4-methoxy-benzoic acid methyl ester

Chemical Property:

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Technology Process of 3-((E)-5-Carboxy-3-methyl-pent-2-enyl)-5-chloro-2-hydroxy-4-methoxy-benzoic acid methyl ester

There total 12 articles about 3-((E)-5-Carboxy-3-methyl-pent-2-enyl)-5-chloro-2-hydroxy-4-methoxy-benzoic acid methyl ester 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:

: 5446-02-6
4-methoxymethylsalicylate

: 171826-77-0
3-((E)-5-Carboxy-3-methyl-pent-2-enyl)-5-chloro-2-hydroxy-4-methoxy-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 93 percent / SO₂Cl₂ / CH₂Cl₂ / 40.5 h / Heating

2: 90 percent / K₂CO₃ / acetone / 7.25 h / Heating

3: 51 percent / 4 h / 210 °C

4: 1.) O₃, MeOH, 2,) PPh₃ / 1.) CH₂Cl₂, -76 deg C, 50 min, 2.) CH₂Cl₂, MeOH, -76 deg C, 20 min

5: 96 percent / benzene / 8 h / Heating

6: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 1 h / Ambient temperature

7: 97 percent / NaBH₄ / methanol / 0 - 20 °C

8: 83 percent / N,N-diisopropylethylamine, CBr₄, Ph₃P / CH₂Cl₂ / 12.33 h / -76 - 20 °C

9: 1.) NaH / 1.) DMF, RT, 20 min, 2.) DMF, RT, 14 h

10: TFA / CH₂Cl₂ / 1.25 h / 0 - 20 °C

11: HCO₂H / 7 h / Ambient temperature

12: 1 h / 150 °C

With methanol; sodium tetrahydroborate; formic acid; sulfuryl dichloride; carbon tetrabromide; sodium hydride; potassium carbonate; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; In methanol; dichloromethane; acetone; benzene;
DOI:10.1021/jm9501339

Reference yield:

: 171826-80-5
methyl 5-chloro-2-hydroxy-4-methoxybenzoate

: 171826-77-0
3-((E)-5-Carboxy-3-methyl-pent-2-enyl)-5-chloro-2-hydroxy-4-methoxy-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 90 percent / K₂CO₃ / acetone / 7.25 h / Heating

2: 51 percent / 4 h / 210 °C

3: 1.) O₃, MeOH, 2,) PPh₃ / 1.) CH₂Cl₂, -76 deg C, 50 min, 2.) CH₂Cl₂, MeOH, -76 deg C, 20 min

4: 96 percent / benzene / 8 h / Heating

5: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 1 h / Ambient temperature

6: 97 percent / NaBH₄ / methanol / 0 - 20 °C

7: 83 percent / N,N-diisopropylethylamine, CBr₄, Ph₃P / CH₂Cl₂ / 12.33 h / -76 - 20 °C

8: 1.) NaH / 1.) DMF, RT, 20 min, 2.) DMF, RT, 14 h

9: TFA / CH₂Cl₂ / 1.25 h / 0 - 20 °C

10: HCO₂H / 7 h / Ambient temperature

11: 1 h / 150 °C

With methanol; sodium tetrahydroborate; formic acid; carbon tetrabromide; sodium hydride; potassium carbonate; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; In methanol; dichloromethane; acetone; benzene;
DOI:10.1021/jm9501339

Reference yield:

: 171826-82-7
methyl 2-(allyloxy)-5-chloro-4-methoxybenzoate

: 171826-77-0
3-((E)-5-Carboxy-3-methyl-pent-2-enyl)-5-chloro-2-hydroxy-4-methoxy-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 51 percent / 4 h / 210 °C

2: 1.) O₃, MeOH, 2,) PPh₃ / 1.) CH₂Cl₂, -76 deg C, 50 min, 2.) CH₂Cl₂, MeOH, -76 deg C, 20 min

3: 96 percent / benzene / 8 h / Heating

4: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 1 h / Ambient temperature

5: 97 percent / NaBH₄ / methanol / 0 - 20 °C

6: 83 percent / N,N-diisopropylethylamine, CBr₄, Ph₃P / CH₂Cl₂ / 12.33 h / -76 - 20 °C

7: 1.) NaH / 1.) DMF, RT, 20 min, 2.) DMF, RT, 14 h

8: TFA / CH₂Cl₂ / 1.25 h / 0 - 20 °C

9: HCO₂H / 7 h / Ambient temperature

10: 1 h / 150 °C

With methanol; sodium tetrahydroborate; formic acid; carbon tetrabromide; sodium hydride; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; In methanol; dichloromethane; benzene;
DOI:10.1021/jm9501339