Benzyl Bromide → HCID 11108273, compound

HRID 1278515Notes

Reaction equation

HRID 1278515 reaction equation
[O:1]=[C:2]1[O:8][C@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[C:5]([OH:6])=[C:3]1[OH:4].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CS(C)=O.ClCCl>[CH2:19]([O:6][C:5]1[C@@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[O:8][C:2](=[O:1])[C:3]=1[OH:4])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 54670067L-Ascorbic Acid

Product 1

HCID 11108273HCID 11108273, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Ascorbic acid (10 g, 56.8 mmol) was dissolved in 60 ml of dimethylsulfoxide, followed by addition of cesium carbonate (9.25 g, 28.4 mmol). After 20 minutes, benzyl bromide (6.75 ml, 56.8 mmol) was added to the reaction mixture and heated to 50° C. for 18 hours. The reaction mixture was cooled down to the room temperature and diluted with 150 ml of dichloromethane to produce a solid. After filtration, the filtrate was concentrated under reduced pressure and purified by column chromatography on silica gel to give 7.2 g of the 3-O-benzyl ascorbic acid (yield 48%).

Workup

  1. temperatureThe reaction mixture was cooled down to the room temperature
  2. customto produce a solid
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-86563f1273724ae28f3453b117a169f3
Source dataset
uspto-grants-2002_09
Patent number
US06444144B1

Reaction notes

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