Thionyl Chloride → 2-(Chloromethyl)-1,3-diethylbenzene

HRID 1256201Notes

Reaction equation

HRID 1256201 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[CH2:11]O)[CH3:2].O=S(Cl)[Cl:15]>CN(C=O)C.C1(C)C=CC=CC=1>[Cl:15][CH2:11][C:4]1[C:3]([CH2:1][CH3:2])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 13383922(2,6-Diethylphenyl)methanol

Product 1

HCID 183574492-(Chloromethyl)-1,3-diethylbenzeneYield 97.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of (2,6-diethylphenyl)methanol (1.83 g, 11.1 mmol), toluene (20 mL) and DMF (6 drops) was added SOCl2 (2.1 g, 1.6 eq). The resulting solution was stirred at RT (1 h). After evaporating to dryness, the residue was taken up in heptane (˜50 mL) and washed with water (˜5 mL), dried (Na2SO4), filtered and evaporated to give 1.97 g (yield of 97%) of title product. 1H NMR (300 MHz, CDCl3) δ 1.28 (t, 6H), 2.79 (q, 2H), 4.70 (s, 2H), 7.09 (d, 2H), 7.20 (m, 1H).

Workup

  1. customAfter evaporating to dryness
  2. washwashed with water (˜5 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-690dc8a3ed9a4a57a11db157955580cd
Source dataset
uspto-grants-2013_06
Patent number
US08461153B2

Reaction notes

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