Thionyl Chloride → (2-Iodo-3-methylphenyl)methanol
Reaction equation
S(Cl)(Cl)=O.[I:5][C:6]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](O)=[O:9]>>[I:5][C:6]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:7]=1[CH2:8][OH:9]Participants
3
Conditions
- Temperature
- 50 °C
Procedure
Thionyl chloride [5 mL] was added to 2-iodo-3-methyl-benzoic acid (2.00 g, 7.63 mmol) at room temperature and heated to 50° C. for 1 hour. The solution was then cooled and evaporated. The crude residue was dissolved in ethyl acetate, washed with brine and dried with magnesium sulfate. The crude product was then dissolved in THF [5 mL] and a 1M solution of lithium aluminum hydride [10.7 mL] was added at room temperature and stirred for 1 hour. Water [0.1 mL] and 15% NaOH [0.1 mL] were added followed by evaporation. Column chromatography (50% EtOAc in hexanes) of the residue yielded the title compound (0.50 g, 26%) as a solid. 1H-NMR (CDCl3): δ 3.20 (t, 2H, J=7.6 Hz), 2.98 (s, 3H), 2.52 (t, 2H, J=7.2 Hz), 2.09 (m, 2H).
Workup
- temperatureThe solution was then cooled
- customevaporated
- dissolutionThe crude residue was dissolved in ethyl acetate
- washwashed with brine
- dry with materialdried with magnesium sulfate
- dissolutionThe crude product was then dissolved in THF [5 mL]
- additiona 1M solution of lithium aluminum hydride [10.7 mL] was added at room temperature
- additionWater [0.1 mL] and 15% NaOH [0.1 mL] were added
- customfollowed by evaporation
Sources & evidence
- ORD record
- ord-034d67d5167c4a4ab724b7739680538f
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07138530B2
Reaction notes
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