HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → 4,4'-Tolan-dicarboxylic acid di-tert.-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | 2-Methyl-3-butyn-2-ol | HCID 8258 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Tert-butyl 4-bromobenzoate | HCID 11334366 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Benzyl triethylammonium chloride | HCID 66133 | — |
| Product | 4,4'-Tolan-dicarboxylic acid di-tert.-butyl ester | HCID 14847526 | — |
Reaction Steps
A mixture of 514 g of 4-bromobenzoic acid tert.-butyl ester, 88.25 g of 2-methyl-3-butyn-2-ol and 74.5 g of triphenylphosphine in 1250 ml of toluene is added to 7.1 g of benzyl triethylammonium chloride, 9.55 g of copper(I)iodide and 14 g of (Pφ3)2PdCl2 and the reaction mixture is stirred at reflux for 48 hours after the addition of 750 ml of 5.5 N NaOH. The organic phase is separated off, dried and concentrated by evaporation. 430 g of moist crude product are stirred up in 550 ml of methanol and suction filtered. 248 g of 4,4'-tolan-dicarboxylic acid di-tert.-butyl ester are obtained and may be further purified by recrystallisation from acetonitrile.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05068300 |
| Source dataset | uspto-grants-1991_11 |
| ORD ID | ord-11b7ead8b8d24e0d8968afbee00b18a3 |
| Source note | uspto-grants-1991_11 |