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

HRID 503251Notes

Reaction equation

HRID 503251 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-7aeb915deb404a8baa4eb9f27a305118
Source dataset
uspto-grants-2010_08
Patent number
US07776905B2

Reaction notes

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