Hydrochloric Acid → HCID 23172753, compound

Temperature

-10 °C

(Formula II, R1=CH3OC(O)—, R2=benzyl). A slow stream of hydrogen chloride gas was passed for 4 h through a solution of 2-benzyloxy-3-bromopropionitrile (16.75 g) in methanol (2.38 g) and ether (66 ml) which was maintained at −10° C. The mixture was allowed to stand at 5° C. overnight, and then ice was added in small portions to the mixture at 0° C. After 20 min of stirring, the mixture was poured into water and the product was extracted with ether, washed with water and aqueous sodium bicarbonate, and dried (MgSO4). After the solvent was removed, the crude product was recrystallized from ether/CH2Cl2 to afford, after a first crop of crystals of 2-benzyloxy-3-bromopropanamide, the required intermediate, methyl 2-benzyloxy-3-bromopropanoate. This bromoester was treated with DBN/potassium carbonate as described above to yield methyl α-benzyloxyacrylate, mp 44.5-45.5° C. (from hexane); 1H NMR δ 3.80 (3H, s), 4.63 (1H, d, J 3 Hz), 4.83 (2H, s), 5.37 (1H, d, J 3Hz), 7.33 (5H, s); IR 1740 cm−1. Ketals of alkyl pyruvates, prepared-according to the directions in The Journal of Organic Chemistry, 1967, 32,1615, also may be converted to α-alkoxyacrylates by an acidic catalyst, as described in Chemische Berichte, 1911, 44, 3514.

1. additionice was added in small portions to the mixture at 0° C
2. extractionthe product was extracted with ether
3. washwashed with water and aqueous sodium bicarbonate
4. dry with materialdried (MgSO4)
5. customAfter the solvent was removed
6. customthe crude product was recrystallized from ether/CH2Cl2
7. customto afford

ORD record

ord-0de192eb3fe94b97b8edbf15349515c2

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06197905B1