Hydrochloric Acid → p-Toluenesulfonic acid

HRID 479911Notes

Reaction equation

HRID 479911 reaction equation
C[O-].[Na+].[CH3:4][C:5]([CH3:8])([O-])[CH3:6].[K+].[CH2:10]([Li])[CH2:11][CH2:12]C.Cl.[S:16](=O)(=[O:19])([OH:18])[OH:17]>C(O)=O.C(OCC)C.C1COCC1>[C:5]1([CH3:8])[CH:6]=[CH:12][C:11]([S:16]([OH:19])(=[O:18])=[O:17])=[CH:10][CH:4]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 10942334Sodium MethoxideHCID 23665647Potassium tert-butoxideHCID 178418339Butyllithium

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

The synthetic intermediate (13) is reacted with triphenylphophonium halide (32) in the same manner as described above in an ether base solvent such as THF and diethyl ether in the presence of a base such as sodium methylate, potassium t-butoxide (t-BuOK) and butyl lithium and then dehydrated by virtue of an action of a mineral acid such as hydrochloric acid and sulfuric acid or an organic acid such as formic acid and p-toluenesulfonic acid, whereby an aldehyde compound (34) is obtained. The compound (34) is reacted with a diol compound (35) by virtue of an action of a mineral acid such as hydrochloric acid and sulfuric acid or an organic acid such as formic acid and p-toluenesulfonic acid, whereby a dioxane ring can be introduced as shown in a compound (36):

Sources & evidence

ORD record
ord-b061aa9f81724d24a801cfbc000e9eb3
Source dataset
uspto-grants-2003_11
Patent number
US06649227B2

Reaction notes

Loading…