Hydrochloric Acid → 2-(4-Chlorophenyl)-2-methylpropanal

HRID 54270Notes

Reaction equation

HRID 54270 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)([CH3:5])[CH2:3][OH:4].C(N(CC)CC)C.Cl>CS(C)=O>[CH3:5][C:2]([C:6]1[CH:7]=[CH:8][C:9]([Cl:12])=[CH:10][CH:11]=1)([CH3:1])[CH:3]=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 130345572-(4-Chlorophenyl)-2-methylpropanol

Product 1

HCID 114353342-(4-Chlorophenyl)-2-methylpropanalYield 55.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirring solution of 41.7 grams (0.226 mole) of 2-methyl-2-(4-chlorophenyl)propanol in 100 mL of dimethyl sulfoxide is added 126 mL (0.904 mole) of triethylamine. A solution of 63.0 grams (0.452 mole) of triethylamine-sulfur trioxide complex in 300 mL of dimethyl sulfoxide is then added portionwise during a 15 minute period. Upon completion of addition, the reaction mixture is stirred at ambient temperature for about five hours. The reaction mixture is then poured into about 500 mL of ice, and made acidic with aqueous 2N hydrochloric acid. The mixture is then extracted with two 100 mL portions of diethyl ether. The combined extracts are dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 22.9 grams of 2-methyl-2-(4-chlorophenyl)propanaldehyde. The NMR spectrum is consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. extractionThe mixture is then extracted with two 100 mL portions of diethyl ether
  3. dry with materialThe combined extracts are dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-ffe278f42544409d9d0cfd5057b2022e
Source dataset
uspto-grants-1997_04
Patent number
US05622954

Reaction notes

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