US 11,882,852 B2
Process of producing alpha-hydroxy compounds and uses thereof
Søren Tolborg, Farum (DK); Juan Salvador Martínez Espín, Copenhagen (DK); and Esben Taarning, Frederiksberg (DK)
Assigned to HALDOR TOPSØE A/S, Kgs. Lyngby (DK)
Appl. No. 16/965,519
Filed by HALDOR TOPSØE A/S, Kgs. Lyngby (DK)
PCT Filed Jan. 23, 2019, PCT No. PCT/EP2019/051632
§ 371(c)(1), (2) Date Jul. 28, 2020,
PCT Pub. No. WO2019/154624, PCT Pub. Date Aug. 15, 2019.
Claims priority of application No. PA 2018 00064 (DK), filed on Feb. 9, 2018.
Prior Publication US 2021/0045414 A1, Feb. 18, 2021
Int. Cl. C07C 51/00 (2006.01); C07C 51/44 (2006.01); C07C 227/08 (2006.01); C07C 51/16 (2006.01); C07C 67/39 (2006.01); C07C 319/20 (2006.01); A23K 20/142 (2016.01); B01J 29/70 (2006.01); C07C 53/126 (2006.01); C07C 57/30 (2006.01); C08G 63/06 (2006.01); C08K 5/101 (2006.01); C08K 5/3417 (2006.01); C08K 5/3445 (2006.01)
CPC A23K 20/142 (2016.05) [B01J 29/7049 (2013.01); B01J 29/7057 (2013.01); C07C 51/00 (2013.01); C07C 51/16 (2013.01); C07C 51/44 (2013.01); C07C 53/126 (2013.01); C07C 57/30 (2013.01); C07C 67/39 (2013.01); C07C 227/08 (2013.01); C07C 319/20 (2013.01); C08G 63/06 (2013.01); C08K 5/101 (2013.01); C08K 5/3417 (2013.01); C08K 5/3445 (2013.01)] 17 Claims
 
1. A process for producing an alpha-hydroxy reaction product of the formula I:
(R)CH(R′)—CHOH—COOR″  (I)
wherein
R is —H or —CH3;
R′ is —CH3, —CH2CH3, —CH(CH3)2, —C6H5, —CH2SCH3, —C8H6N or —C3H3N2; and
R″ is —H, —CH2CH3, —CH(CH3)2, —CH2CH2CH3, —CH2CH2CH2CH3, —CH2CH(CH3)2, or —C(CH3)3 comprising the steps of:
a) Providing provising a first compound of the formula II:
OHCH2—CHO   (II)
b) providing a second compound of the formula III:
R—CO—R′  (III)
wherein
R and R′ have the meanings as defined above; and
c) reacting the first compound with the second compound in the presence of a Lewis acid catalyst and a reagent R″OH to provide the alpha-hydroxy reaction product, wherein R″ has the meaning as defined above, wherein the Lewis acid catalyst comprises one or more active metals selected from the group consisting of Sn, Ti, Pb, Zr, Ge and Hf.