Benzyl Chloride → HCID 86730353, compound

HRID 1427052Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:19]=[O:20]>C(O)C.Cl.C(OCC)(=O)C.O>[CH2:7]([O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:19]=[O:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Potassium carbonate (14.7 g, 106 mmol) and benzyl chloride (12.2 mL, 106 mmol) were added to a solution of 3-hydroxy-4-(3-methoxypropoxy)benzaldehyde described in Production Example 32-1 (17.2 g, 81.7 mmol) in ethanol (200 mL) under nitrogen atmosphere at room temperature, and the mixture was stirred under a thermal condition of 90° C. for 2 hours. The reaction liquid was cooled to 0° C., and the mixture was diluted with 2 M hydrochloric acid, ethyl acetate, and water. The organic layer was washed with a saturated saline solution and then dried over anhydrous magnesium sulfate. The drying agent was separated by filtration and then the filtrate was concentrated under vacuum. The residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=4:1-3:7) to obtain the title compound (19.8 g, 81%).

Workup

customThe reaction liquid
temperaturewas cooled to 0° C.
washThe organic layer was washed with a saturated saline solution
dry with materialdried over anhydrous magnesium sulfate
customThe drying agent was separated by filtration
concentrationthe filtrate was concentrated under vacuum
customThe residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=4:1-3:7)

Sources & evidence

ORD record: ord-d6c507076459472b8f2948312b0df6cc
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933099B2

Reaction notes

Loading…