Methyl Ethyl Ketone → 1-(2,5-Bis(benzyloxy)phenyl)ethanone

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20](=O)([O-])[O-].[K+].[K+].C1O[CH2:42][CH2:41]OCCOCCOCCOCCOC1.[CH3:44][C:45](=O)[CH2:46][CH3:47]>>[CH2:12]([O:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:20][C:42]2[CH:41]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Reactant 5

HCID 6569Methyl Ethyl Ketone

HCID 7503Benzyl Chloride

HCID 102792-Acetylhydroquinone

HCID 11430Potassium Carbonate

HCID 2855718-Crown-6

Product 1

HCID 127460231-(2,5-Bis(benzyloxy)phenyl)ethanone

Procedure

A mixture of 1-(2,5-dihydroxyphenyl)ethanone (3.16 g), benzyl chloride (7.04 g), potassium carbonate (12.4 g) and 18-Crown-6 (30 mg) in 2-butanone (50 ml) was heated under reflux for 5 hrs. After cooling the precipitate was filtered off. The filtrate was evaporated to dryness under reduced pressure and ether (50 ml) was added to it. The solution was washed twice with dilute sodium hydroxide solution, twice with dilute hydrochloric acid, dried over sodium sulphate and substantially evaporated to dryness under reduced pressure. The residue was triturated with cold n-heptane (30 ml), and the precipitate was filtered off with suction filtration giving after drying 2.85 g of 1-[2,5-Bis(benzyloxy)phenyl]ethanone. 1H NMR (400 MHz, DMSO-d6) δ=2.50 (s, 3H), 5.08 (s, 2H), 5.18 (s, 2H), 7.20-7.50 (m, 13H).