Hydrochloric Acid → HCID 22251526, compound

HRID 1611889Notes

Reaction equation

HRID 1611889 reaction equation
C[C:2]1[C:3]([CH3:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH3:10][S:11]([CH3:13])=O.[ClH:14].[CH3:15]O>>[Cl-:14].[OH:8][C:4]1[C:3]([CH3:9])=[CH:2][C:7]([S+:11]([CH3:13])[CH3:10])=[CH:6][C:5]=1[CH3:15]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 887MethanolHCID 106872,3-Dimethylphenol

Product 1

HCID 22251526HCID 22251526, compound

Procedure

61 g of dimethylphenol (0.5 mole), 39 g (0.5 mole) of dimethylsulfoxide (DMSO), and 400 ml of methanol were placed in a 1 liter round bottom flask equipped with a thermometer and a condenser. The mixture was cooled in a liquid nitrogen-isopropyl alcohol bath while hydrogen chloride gas was bubbled in at 10° C. for 6 hours. A precipitate was formed and a part of the methanol was removed by rotavap. The crystals were filtered and washed with ether several times. The solid product gave the following analytical results 1H NMR(Acetone-d6), 2.34 (s, 6H, 2CH3); 3.23 (s, 6H, 2CH3); 7.80 (s, 2H, aromatic).

Workup

  1. customequipped with a thermometer and a condenser
  2. customwas bubbled in at 10° C. for 6 hours
  3. customA precipitate was formed
  4. customa part of the methanol was removed by rotavap
  5. filtrationThe crystals were filtered
  6. washwashed with ether several times
  7. customThe solid product gave the following
  8. customanalytical results 1H NMR(Acetone-d6), 2.34 (s, 6H, 2CH3); 3.23 (s, 6H, 2CH3); 7.80 (s, 2H, aromatic)

Sources & evidence

ORD record
ord-6fa8e32f080a4e14920354520b3e9b95
Source dataset
uspto-grants-2006_01
Patent number
US06991888B2

Reaction notes

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