ChemicalBook CAS DataBase List (2-CHLOROPHENYL)ACETALDEHYDE

(2-CHLOROPHENYL)ACETALDEHYDE synthesis

6synthesis methods

Product Name:(2-CHLOROPHENYL)ACETALDEHYDE
CAS Number:4251-63-2
Molecular formula:C8H7ClO
Molecular Weight:154.59

57486-68-7
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$10.00/5g

4251-63-2
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$185.00/500mg

Yield: 100%

Reaction Conditions:

with diisobutylaluminium hydride in dichloromethane;toluene at -78; for 1 h;Inert atmosphere;

Steps:

28.1 Step 1: 2-(2-Chlorophenyl)acetaldehyde:
A solution of methyl 2-(2-chlorophenyl)acetate (3.0 g, 16 mmol) in anhydrous dichloromethane (30 mL) was cooled to -78 °Cfollowed by the dropwise addition of DIBAL-H (1 M in toluene, 16.3 mL, 16 mmol) over a period of 30 mm. The reaction mixture was stirred at -78 °C under a nitrogen atmosphere for a further 30 mm, then quenched by the addition of methanol (15 mL) and poured into saturatedsodium potassium tartrate (aq) solution (100 mL) . The resulting mixture was stirred vigorously for 1 h and extracted into dichloromethane (3 x 50 mL) . The combined organic phases were dried over Na2504, filtered and concentrated to dryness under reduced pressure to givethe title compound (2.65 g, quantitative yield) as a pale yellow oil. ‘H NMR (500 MHz, CDC13) : 6 9.76 (t, 1H), 7.41-7.46 (m, 1H), 7.22-7.29 (m, 3H), 3.85 (d, 2H)

References:

ALMAC DISCOVERY LIMITED;ROUNTREE, James Samuel Shane;O'DOWD, Colin Roderick;BURKAMP, Frank;BELL, Mark Peter WO2015/19037, 2015, A1 Location in patent:Page/Page column 95

2039-87-4 Synthesis