Methanol → 2,2-Dimethyl-4-((phenylmethoxy)methyl)-1,3-dioxolane

HRID 656314

Reaction equation

[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.CO.C[O-].[Na+].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH2:15]([O:8][CH2:7][CH:5]1[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 1000 ml round-bottom flask fitted with a thermometer, a nitrogen-introducing tube, and a stirrer were added 132.2 g (1.0 mol) of 2,2-dimethyl-1,3-dioxolane-4-methanol, 231.4 g (1.2 mol) of a 28% methanol solution of sodium methoxide, and 500 ml of toluene. With introducing nitrogen thereinto, the toluene was refluxed under reduced pressure for 1 hour to remove the methanol by distillation. With maintaining the solution at 80° C., 126.6 g (1.0 mol) of benzyl chloride was added dropwise over a period of 2 hours using a dropping funnel, followed by further 2 hours of the reaction. The reaction solution was subjected to solvent removal and purification by distillation (b.p. 93-95° C./266 Pa) to obtain 4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane.

Workup

customTo a 1000 ml round-bottom flask fitted with a thermometer
additiona nitrogen-introducing tube, and a stirrer
customto remove the methanol
distillationby distillation
customfollowed by further 2 hours of the reaction
customThe reaction solution was subjected to solvent removal and purification by distillation (b.p. 93-95° C./266 Pa)

Sources & evidence

ORD record: ord-809ce9f051b740c98405f973084c81ac
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071712B2

Linked notes

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