2,4-Dihydroxybenzaldehyde → 2,4-Bis(benzyloxy)benzaldehyde

HRID 922278Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[C:8](O)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:11]([O-:14])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C>[CH2:17]([O:1][C:2]1[CH:9]=[C:8]([O:14][CH2:11][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:3]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 250 mL RB flask fitted with magnetic stirrer was charged 100 mL of acetonitrile. To the stirred solvent was added 2,4-dihydroxybenzaldehyde (10.0 g, 72.0 mmol) and K2CO3 (19.87 g, 144.0 mmol). Then it was stirred for 15 min, slowly was added benzylbromide (12.38 g, 72.0 mmol), the RM was heated to 80° C. for 3 h. Then, the solvent was removed under reduced pressure and the compound was extracted with ethyl acetate (50 mL×3). The organic layer washed with water and saturated brine solution and dried over anhydrous Na2SO4 and evaporated to dryness to get the crude product. The crude material was purified by silica gel column chromatography using ethyl acetate and petroleum ether as elutants to obtain the product (2.3 g, yield: 10.03%).

Workup

customTo a 250 mL RB flask fitted with magnetic stirrer
customThen, the solvent was removed under reduced pressure
extractionthe compound was extracted with ethyl acetate (50 mL×3)
washThe organic layer washed with water and saturated brine solution
dry with materialdried over anhydrous Na2SO4
customevaporated to dryness
customto get the crude product
customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-cde73a44ebdc400dab548a4db9baf053
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278915B2

Reaction notes

Loading…