Thionyl Chloride → 6-(Chloromethyl)-4-methoxy-2H-1,3-benzodioxole

HRID 17921Notes

Reaction equation

HRID 17921 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[C:5]([CH2:12]O)[CH:4]=1.C([O-])(O)=O.[Na+].O=S(Cl)[Cl:21]>>[Cl:21][CH2:12][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 602667(7-Methoxy-1,3-benzodioxol-5-yl)methanol

Product 1

HCID 139140006-(Chloromethyl)-4-methoxy-2H-1,3-benzodioxoleYield 94%

Procedure

To a solution of SOCl2 (150 mL) was added (7-methoxybenzo[d][1,3]dioxol-5-yl)methanol (9.0 g, 54 mmol) in portions at 0° C. The mixture was stirred for 0.5 h. The excess SOCl2 was evaporated under reduced pressure to give the crude product, which was basified with sat. aq. NaHCO3 to pH ˜7. The aqueous phase was extracted with EtOAc (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated to give 6-(chloromethyl)-4-methoxybenzo[d][1,3]dioxole (10.2 g 94%), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 6.58 (s, 1H), 6.57 (s, 1H), 5.98 (s, 2H), 4.51 (s, 2H), 3.90 (s, 3H).

Workup

  1. customThe excess SOCl2 was evaporated under reduced pressure
  2. customto give the crude product, which
  3. extractionThe aqueous phase was extracted with EtOAc (100 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-cf53d13c4eaa455b9dfaea1dda090451
Source dataset
uspto-grants-2010_06
Patent number
US07741321B2

Reaction notes

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