Water → 8-(2-Propenyloxy)-1,4-dioxaspiro[4.5]decane
Reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:14](Br)[CH:15]=[CH2:16].O>CN(C)C=O>[CH2:16]([O:11][CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[CH:15]=[CH2:14]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
23.7 g (150 mmole) 1,4-dioxa-spiro[4.5]decan-8-ol were dissolved in 120 ml absolute dimethylformamide under a nitrogen atmosphere. After adding 7.9 g of 50% sodium hydride in mineral oil (165 mmole), the mixture was stirred for 1 hour at 20° C. After adding 14.3 ml allyl bromide (165 mmole), the mixture was heated to 70° C. and stirred for 1 hour. Thereafter it was treated with 160 ml water and was extracted at 10° C.-15° C., three times with ether, once with water and once with saturated sodium chloride solution. After removing the solvent by distillation, 24 g of crude product (81% theoretical) were obtained.
Workup
- temperaturethe mixture was heated to 70° C.
- stirringstirred for 1 hour
- extractionwas extracted at 10° C.-15° C.
- customAfter removing the solvent
- distillationby distillation
Sources & evidence
- ORD record
- ord-5fc74dfa42f948c5875825b728ac3ebc
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05801201
Reaction notes
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