Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 1-(Chloromethoxy)-2-methoxyethane | HCID 77590 | — |
| Reactant | Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylate | HCID 1490289 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 21920147 | HCID 21920147 | 87% |
Reaction Steps
10 g (43.8 mmol) of 4′-hydroxybiphenyl-4-carboxylic acid methyl ester, 100 ml of THF and 150 ml of DMF are introduced in order and under a nitrogen stream into a 500 ml three-necked flask. 1.93 g (48.2 mmol) of NaH at 60% in oil are added in small portions and the mixture is stirred at room temperature for 15 hours. 5.75 ml of 1-chloromethoxy-2-methoxyethane are added dropwise, and the mixture is stirred at room temperature for 30 minutes. The reaction medium is poured over a 1N HCl solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulphate. After filtration and evaporation 12 g of 4′-(2-methoxyethoxymethoxy)biphenyi-4-carboxylic acid methyl ester are obtained in the form of a beige powder after filtration and evaporation (yield=87%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07122564B2 |
|---|
| Source dataset | uspto-grants-2006_10 |
|---|
| ORD ID | ord-b88fd896b298474f86a8d4af67832117 |
|---|
| Source note | uspto-grants-2006_10 |
|---|