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

HRID 1908341Notes

Reaction equation

HRID 1908341 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 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-e1224ff03b754b93ab71d40f3d792144
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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