Acetone → HCID 10932381, compound
Reaction equation
[OH:1][CH2:2][C:3]([CH2:10][OH:11])([CH2:7][CH:8]=[CH2:9])[CH2:4][CH:5]=[CH2:6].C(OC)(OC)OC.[CH3:19][C:20]([CH3:22])=O>S(=O)(=O)(O)O>[CH2:4]([C:3]1([CH2:7][CH:8]=[CH2:9])[CH2:10][O:11][C:20]([CH3:22])([CH3:19])[O:1][CH2:2]1)[CH:5]=[CH2:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
There were put 15.2 g of 4,4-bis(hydroxymethyl)-1,6-heptadiene prepared above, 42.5 mL of trimethyl orthoformate manufactured by Tokyo Chemical Industry Co., Ltd., and 97 mL of dry acetone manufactured by Kanto Chemical Co., Inc. in a 200 mL round-bottom flask. To the resultant mixture, a few drops of concentrated sulfuric acid were added gradually, and the mixture was refluxed for 4 hours. The reaction mixture was extracted with ether, and the extract was washed with saturated aqueous sodium bicarbonate, and was further washed with a saturated sodium chloride solution. The washed extract was dried over anhydrous magnesium sulfate manufactured by Nacalai Tesque, Inc. The dried ether solution was subjected to evaporation to remove ether contained therein. The obtained liquid was distilled in vacuo, thereby obtaining 16.2 g of 5,5-diallyl-2,2-dimethyl-1,3-dioxane as a colorless and oily fraction at 45° C. under a pressure of 4 mmHg.
Workup
- temperaturethe mixture was refluxed for 4 hours
- extractionThe reaction mixture was extracted with ether
- washthe extract was washed with saturated aqueous sodium bicarbonate
- washwas further washed with a saturated sodium chloride solution
- extractionThe washed extract
- dry with materialwas dried over anhydrous magnesium sulfate
- customThe dried ether solution was subjected to evaporation
- customto remove ether
- distillationThe obtained liquid was distilled in vacuo
Sources & evidence
- ORD record
- ord-942074d3167b4bd09dbf90a648b4dda5
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07964691B2
Reaction notes
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