Hydrochloric Acid → 3-Fluoro-6-(phenylthio)-benzyl alcohol
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][CH:10]=1)[C:5](O)=[O:6].Cl>O1CCCC1.C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:8]([S:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:9][CH:10]=1)[CH2:5][OH:6]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
144 g of 3-fluoro-6-(phenylthio)-benzoic acid in 1000 ml of tetrahydrofuran is treated dropwise under a nitrogen atmosphere and under reflux with a 70% sodium-dihydro-bis(2-methoxyethoxy)-aluminate solution in benzene. The mixture is held under reflux for a further 2 hours. After the addition of 400 ml of benzene, the mixture is cooled to 20° C, acidified with 435 ml of 3-N hydrochloric acid and subsequently treated with 600 ml of concentrated hydrochloric acid. The organic phase is washed with water, dried over sodium sulphate and evaporated. There is obtained 3-fluoro-6-(phenylthio)-benzyl alcohol as a thick oil.
Workup
- temperatureunder reflux for a further 2 hours
- washThe organic phase is washed with water
- dry with materialdried over sodium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-d9ed0b9519ef4b07912022ebda87c720
- Source dataset
- uspto-grants-1977_02
- Patent number
- US04006144
Reaction notes
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