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| CAS No.: | 4925-88-6 |
|---|---|
| Name: | 2,5-DIMETHOXY-4-METHYLBENZALDEHYDE |
| Molecular Structure: | |
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| Formula: | C10H12O3 |
| Molecular Weight: | 180.203 |
| Synonyms: | 2,5-Dimethoxy-4-methyl-benzaldehyde; |
| Density: | 1.089g/cm3 |
| Melting Point: | 82-86℃ |
| Boiling Point: | 307.5oC at 760 mmHg |
| Flash Point: | 130.7oC |
| Solubility: | Soluble in dichloromethane, dimethyl sulfoxide and methanol. Slightly soluble in water. |
| PSA: | 35.53000 |
| LogP: | 1.82470 |

2,5-dimethoxy toluene


N-methyl-N-phenylformamide


2,5-dimethoxy-4-methylbenzaldehyde

| Conditions | Yield |
|---|---|
| Stage #1: N-methyl-N-phenylformamide With trichlorophosphate at 20℃; for 0.833333h; Inert atmosphere; Stage #2: 2,5-dimethoxy toluene at 70℃; for 1h; Inert atmosphere; | 86% |
| Stage #1: N-methyl-N-phenylformamide With trichlorophosphate at 20℃; for 0.666667h; Stage #2: 2,5-dimethoxy toluene at 50℃; for 6h; Stage #3: With sodium acetate; sodium hydrogensulfite more than 3 stages; | 67% |
| (i) POCl3, (ii) /BRN= 2045336/; Multistep reaction; | |
| With trichlorophosphate at 0 - 80℃; for 1h; | |
| Stage #1: N-methyl-N-phenylformamide With trichlorophosphate at 20℃; for 4h; Stage #2: 2,5-dimethoxy toluene at 70℃; for 2h; |

2,5-dimethoxy toluene


N,N-dimethyl-formamide


2,5-dimethoxy-4-methylbenzaldehyde

| Conditions | Yield |
|---|---|
| With trichlorophosphate at 80℃; for 8h; | 85.9% |
| With trichlorophosphate In 1,2-dichloro-ethane at 80℃; for 12h; Vilsmeier-Haack formylation; | 80% |
| With trichlorophosphate at 60℃; for 24h; Formylation; |

2,5-dihydroxy-4-methylbenzaldehyde


methyl iodide


2,5-dimethoxy-4-methylbenzaldehyde

| Conditions | Yield |
|---|---|
| With potassium carbonate In acetone at 20℃; for 18h; | 80% |
| With potassium carbonate In acetone at 25℃; for 20h; |

2-(2,5-dimethoxy-4-methyl-phenyl)-[1,3]dioxolane

A

2,5-dimethoxy-4-methylbenzaldehyde

| Conditions | Yield |
|---|---|
| With cobalt (III) fluoride In acetonitrile at 20℃; for 0.416667h; Oxidation; Demethylation; | A 20% B 55% |

Dichloromethyl methyl ether


2,5-dimethoxy toluene


2,5-dimethoxy-4-methylbenzaldehyde

| Conditions | Yield |
|---|---|
| With tin(IV) chloride 1.) CH2Cl2, 0 deg C, 1 h, 2.) CH2Cl2, a) 0 deg C, 30 min, b) RT, 1 h; Yield given. Multistep reaction; | |
| Stage #1: 2,5-dimethoxy toluene With titanium tetrachloride In dichloromethane at 20℃; for 2h; Inert atmosphere; Cooling with ice; Stage #2: Dichloromethyl methyl ether In dichloromethane at 20℃; for 2.5h; Inert atmosphere; Cooling with ice; | 9.1 g |

| Conditions | Yield |
|---|---|
| With hydrogenchloride; aluminium trichloride; sulfuric acid 1) tetrachloroethane, 8 h, 65-70 deg C 2) overnight, room temperature 3) steam distillation; Yield given. Multistep reaction; |

2,5-dimethoxy-4-methylphenylmethanol


2,5-dimethoxy-4-methylbenzaldehyde

| Conditions | Yield |
|---|---|
| With selenium(IV) oxide |

| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 82 percent / potassium hydroxide / methanol / 8 h / steam distillation 2: 1) HCl, aluminium chloride 2) aqueous H2SO4 / 1) tetrachloroethane, 8 h, 65-70 deg C 2) overnight, room temperature 3) steam distillation View Scheme |


2,5-dimethoxy toluene


N-methyl-N-phenylformamide


2,5-dimethoxy-4-methylbenzaldehyde

| Conditions | Yield |
|---|---|
| In water |


2,5-dimethoxy-4-methylbenzaldehyde


2-hydroxy-4-methyl-5-methoxybenzaldehyde

| Conditions | Yield |
|---|---|
| With aluminium trichloride; sodium iodide In acetonitrile for 2h; Heating; | 99% |
| With boron trichloride In dichloromethane at -78 - 20℃; | 65% |
| Stage #1: 2,5-dimethoxy-4-methylbenzaldehyde With aluminum (III) chloride; sodium iodide In acetonitrile at 80℃; for 1h; Stage #2: With water In acetonitrile at 0℃; |