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|---|---|
| Verifiedrevid | 477212051 |
| Reference | [1] |
| Pin | 2,6-Dichlorophenol |
2,6-Dichlorophenol is a compound with formula C6H3Cl2OH. It is one of the six isomers of dichlorophenol. It is a colorless solid. Its pKa is 6.78, which is about 100x more acidic than 2-chlorophenol (8.52) and 1000x more acidic than phenol itself (9.95).[2]
Preparation
It can be produced in a multistep process from phenol, which is converted to its 4-sulfonic acid derivative. The resulting phenol sulfonic acid chlorinates at the positions flanking the phenol. Hydrolysis releases the sulfonic acid group.[3]
An alternative synthesis starts with the ethyl ester of 4-hydroxybenzoic acid, which chlorinates at the positions flanking the phenolic center. Ester hydrolysis followed by decarboxylation affords 2,6-dichlorophenol.[4]
References
- ^ 2,6-Dichlorophenol at Sigma-Aldrich
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- ^ D. S. Tarbell; J. W. Wilson; Paul E. Fanta (1949). "2,6-Dichlorophenol". Org. Synth.. 29: 35. doi:10.15227/orgsyn.029.0035
Cited sources
- Haynes, William M. (ed.) (2016). CRC Handbook of Chemistry and Physics. 97th ed. CRC Press. ISBN 9781498754293.