Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | 3-Methylsalicylic Acid | HCID 6738 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | tetrahydrofuran N,N-dimethylformamide | HCID 21974620 | — |
| Product | HCID 19877818 | HCID 19877818 | — |
Reaction Steps
at room temperature, a solution of 100.3 g of 2-hydroxy-3-methylbenzoic acid in 150 ml of DMF/THF (dimethylformamide/tetrahydrofuran, 1:1) is dripped into 43.6 g of sodium hydride (80% strength in white oil) in 350 ml of DMF/THF (1:1). The mixture is stirred for 40 minutes at 60° C. and then 226.5 g of ethyl iodide is dripped in at room temperature. After the addition of a further 250 ml of DMF/THF (1:1) the mixture is stirred for 9 hours at 60°-70° C. The reaction mixture is poured into ice water and extracted with ether. The combined organic phases are washed with water, dried and concentrated. There is obtained 126.3 g of the desired compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05147645 |
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| Source dataset | uspto-grants-1992_09 |
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| ORD ID | ord-c72c1eeecbee464a949c7b4af58a08d3 |
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| Source note | uspto-grants-1992_09 |
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