ChemicalBook CAS DataBase List Methyl 2-chloromethylbenzoate

Methyl 2-chloromethylbenzoate synthesis

9synthesis methods

Product Name:Methyl 2-chloromethylbenzoate
CAS Number:34040-62-5
Molecular formula:C9H9ClO2
Molecular Weight:184.62

67-56-1 Synthesis

67-56-1
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$7.29/5ml-f

87-41-2 Synthesis

87-41-2
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$6.00/10g

34040-62-5
99 suppliers
$25.00/1g

Yield: 100%

Reaction Conditions:

Stage #1:2-benzofuran-1(3H)-one with boron trifluoride diethyl etherate;N-benzyl-N,N,N-triethylammonium chloride in xylene at 100;
Stage #2: with thionyl chloride in xylene at 100 - 132; for 3 h;
Stage #3:methanol at 50 - 60; for 2 h;

Steps:

1.1; 1.2
[Step 1] In a 1-liter 4-neck flask, 643 ml of xylene, 134.1 g (1.0 mole) of phthalide, 18.2 g (0.08 mole) of benzyltriethylammonium chloride and 9.9 g (0.07 mole) of BF₃-ether complex were charged and heated to 100°C. Subsequently, 142.8 g (1.2 moles) of thionyl chloride was dropwise added to the mixture over one hour, for subsequent 2-hour agitation at 125 to 132°C. Until the inner temperature reached 135°C at atmospheric pressure, xylene and excess thionyl chloride (about 350 ml) were distilled off, and then, xylene (about 350 ml) was additionally distilled off under reduced pressure.[Step 2] Eighty and one-tenth grams (80.1 g) of methanol (2.5 moles) was dropwise added to the concentrated residue obtained at the step 1 over one hour. During the term, the solution was retained at the inner temperature of 60°C or less, while the solution was cooled in a water bath. Subsequently, agitation was done at 50°C for one hour, and then, the solution was cooled to 25°C. Then, a solution of 300 ml of toluene added to the reaction solution was dropwise added over 30 minutes to a solution of 70.0 g (0.51 mole) of potassium carbonate dissolved in 300 ml of water. The separated toluene layer was washed in 130 g of aqueous 30% saline, and concentrated under reduced pressure, to obtain 189.2 g of methyl 2-chloromethylbenzoate. The apparent yield was 102.5 %. MS (m/z) 184 (M+)

References:

Sumitomo Chemical Company, Limited EP2058294, 2009, A1 Location in patent:Page/Page column 7-8