Benzyl Bromide → HCID 131729662, compound

HRID 1698294Notes

Reaction equation

[CH2:1]([O:5][C:6]1[C@@:11]([CH2:16][CH:17]([CH2:19][OH:20])[OH:18])([C@H:12]([CH2:14][OH:15])[OH:13])[O:10][C:8](=[O:9])[C:7]=1[OH:21])[CH2:2][CH2:3][CH3:4].C(=O)([O-])O.[Na+].[CH2:27](Br)[C:28]1C=CC=[CH:30][CH:29]=1>CS(C)=O>[CH2:1]([O:5][C:6]1[C@@:11]([CH2:16][CH:17]([CH2:19][OH:20])[OH:18])([C@H:12]([CH2:14][OH:15])[OH:13])[O:10][C:8](=[O:9])[C:7]=1[O:21][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

Under an argon atmosphere, 3-O-butylglyceryl ascorbic acid (3.06 g) obtained in Example 6 was stirred in DMSO (10 mL), and further, sodium hydrogen carbonate (0.84 g) was added. To the mixture, benzyl bromide (2.06 g) was added and the mixture was heated up to 100° C. and stirred for 3 hours, followed by extraction with ethyl acetate. Then, the extracted liquid was dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and 3.52 g of the resultant residue was subjected to silica gel column chromatography. Elution was performed with chloroform/methanol/water(volume ratio:50/3/0.3), and concentration was performed under reduced pressure to obtain 3-O-butylglyceryl-2-O-butyl ascorbic acid (0.95 g).

Workup

extractionfollowed by extraction with ethyl acetate
dry with materialThen, the extracted liquid was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure, and 3.52 g of the resultant residue
washElution
concentrationwas performed with chloroform/methanol/water(volume ratio:50/3/0.3), and concentration

Sources & evidence

ORD record: ord-98ee829698b14c6a8aeb9798102b26e1
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163939B2

Reaction notes

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