Benzyl Bromide → Phenylmethyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate

Temperature

100 °C

A mixture of 2,2-bis(methylol)propionic acid (bisMPA) (18.0 g, 0.134 mol), KOH (85% assay; 8.9 g, 0.135 mol), and DMF (100 mL) was heated to 100° C. for 1 hour (the reaction mixture became a homogenous solution after 0.5 hour reaction). Benzyl bromide (27.6 g, 0.162 mol) was added to the warm solution under stirring, and the reaction was continued at 100° C. for 16 hours. The reaction mixture was cooled down and the solvent was removed under vacuum. Ethyl acetate (120 mL), hexanes (120 mL), and water (80 mL) were added to the residue. The organic layer was retained, washed with water (80 mL), dried over MgSO4 and evaporated. The resulting solid was recrystallized from toluene (30 mL) to give pure benzyl 2,2-bis(methylol)propionate (BnMPA) (19.5 g, 65%). 1H NMR (400 MHz, CDCl3, 22° C.): delta 7.38 (m, 5H, PhH), 5.19 (s, 2H, —OCH2Ph), 3.94 (d, 2H, —CH2OH), 3.73 (d, 2H, —CH2OH), 1.12 (s, 3H, —CH3).

1. customafter 0.5 hour
2. customreaction)
3. temperatureThe reaction mixture was cooled down
4. customthe solvent was removed under vacuum
5. additionEthyl acetate (120 mL), hexanes (120 mL), and water (80 mL) were added to the residue
6. washwashed with water (80 mL)
7. dry with materialdried over MgSO4
8. customevaporated
9. customThe resulting solid was recrystallized from toluene (30 mL)

ORD record

ord-48b3184e18024bdea614d24f8e8274a1

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08470891B2