Benzaldehyde → HCID 14801250, compound
Reaction equation
[CH:1]([F:10])([F:9])[C:2]([F:8])([F:7])[C:3]([F:6])([F:5])[F:4].[Li][C:12]([CH3:15])([CH3:14])C.[CH:16](=[O:23])[C:17]1C=CC=C[CH:18]=1.Cl>CCCCC.CCOCC>[F:7][C:2]([F:8])([C:3]([F:6])([F:5])[F:4])[C:1]([C:14]1[CH:12]=[CH:15][CH:18]=[CH:17][C:16]=1[OH:23])([F:10])[F:9]Participants
Conditions
- Temperature
- -80 °C
Procedure
60 ml of ether and 3.6 g (30 mmol) of 1H-heptafluoropropane were placed in a 4-neck flask fitted with anchor stirrer, dropping funnel, and internal thermometer and the mixture was cooled to −80° C. 9 g (20 mmol) of tert-BuLi as a 15% strength solution in pentane were then added dropwise and the mixture was stirred for another 30 minutes at this temperature. 2.1 g (20 mmol) of benzaldehyde in 10 ml of ether were subsequently added dropwise. After stirring at −80° C. for 2 hours, the yellow solution was allowed to come to room temperature and dilute hydrochloric acid was added. The mixture was extracted three times with ether and the combined organic phases were dried and filtered. Purification by distillation gave heptafluoropropylphenyl alcohol in a yield of 70%.
Workup
- customfitted with anchor stirrer
- stirringAfter stirring at −80° C. for 2 hours
- customto come to room temperature
- extractionThe mixture was extracted three times with ether
- customthe combined organic phases were dried
- filtrationfiltered
- customPurification
- distillationby distillation
Sources & evidence
- ORD record
- ord-9c7e8110ac8c4e01a719cf02ac99a3d9
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06872861B2
Reaction notes
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