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ChemicalBook CAS DataBase List Butanedioic, 1-(chloromethyl)-4-t-butyl ester
432037-43-9

Butanedioic, 1-(chloromethyl)-4-t-butyl ester synthesis

2synthesis methods
49715-04-0 Synthesis
Chloromethyl chlorosulfate

49715-04-0
265 suppliers
$10.00/1g

15026-17-2 Synthesis
Mono-tert-butyl succinate

15026-17-2
149 suppliers
$6.00/1g

-

Yield:432037-43-9 86%

Reaction Conditions:

Stage #1: succinic acid mono-tert-butyl esterwith tetra(n-butyl)ammonium hydrogensulfate;potassium carbonate in dichloromethane at 0; for 0.333333 h;
Stage #2: chlorosulfuric acid chloromethyl ester in dichloromethane at 0; for 3 h;

Steps:

14.1 Example 14.

Step 1: To a mixture of K2CO3 (4.0 g, 28.94 mmol) and TBAHSO4 (240 mg, 0.70 mmol) in water (8 mL) at 0°C was added 13 (2.0 g, 11.48 mmol) in CH2Cl2 (8 mL). The resulting mixture was stirred at 0°C for 20 min, then 14 (1.3 mL, 12.85 mmol) was added and stirred again for 3 h. The organic layer was separated, washed with water (2×5 mL) and saturated brine (5 mL). The CH2Cl2 layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography eluting with 0-100% EtOAc/hexane to obtain the target compound 15 (2.2 g, 86%) as a colorless gum.

References:

CN111344286,2020,A Location in patent:Paragraph 0323-0325

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