Acetaldehyde → 1,3-Dioxolane, 2-methyl-4-phenyl-

HRID 347617

Reaction equation

[C:1]1([CH:7]([OH:10])[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11](OCC)[CH3:12].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)C>O>[CH3:11][CH:12]1[O:10][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][O:9]1

Participants

Conditions

Temperature: 20 °C

Procedure

A 1 l stirrer fitted with reflux condenser, thermometer and dropping funnel was charged with 223 g (1.47 mol) of (±)-1-phenyl-1,2-ethanediol (3) (91% pure according to GC) from Example 1, 100 ml of diethyl ether and 2 g of para-toluenesulfonic acid and cooled to 5–10° C., and, at this temperature, 80.8 g (1.83 mol) of acetaldehyde were added over the course of 30 min. When the dropwise addition was complete, the mixture was then stirred firstly for 4 h at 5–10° C. and for a further 2 h at a maximum of 20° C. After this time, water was added, the organic phase was separated off, the aqueous phase was extracted with 1×100 ml of ether, and the combined organic phases were washed until neutral with sodium carbonate solution and water. Drying over Na2SO4 was then carried out, and the solvent was distilled off under reduced pressure.

Workup

customA 1 l stirrer fitted
temperaturewith reflux condenser
temperaturecooled to 5–10° C.
additionWhen the dropwise addition
customthe organic phase was separated off
extractionthe aqueous phase was extracted with 1×100 ml of ether
washthe combined organic phases were washed until neutral with sodium carbonate solution and water
dry with materialDrying over Na2SO4
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-4e8c8cddc40841dc9725bbbb58e46a5b
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176176B2

Linked notes

Loading…