3-Butyn-1-OL → HCID 20071329, compound
Reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].Br[CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>O>[CH2:1]([O:5][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:2][C:3]#[CH:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3-butyn-1-ol (5.0 g), (4-bromobutyl)benzene (15.0 g), aqueous sodium hydroxide (30 ml, 50% w/v), and TAB (0.6 g) was stirred vigorously for 3 days, treated with water (100 ml) and extracted with ER (2×200 ml). The dried extract was evaporated and the residue was purified by FCC eluting with CX-ER 19:1 to give the title compound as a colourless oil (9.5 g). T.l.c. (CX-ER 9:1) Rf 0.45.
Workup
- extractionextracted with ER (2×200 ml)
- extractionThe dried extract
- customwas evaporated
- customthe residue was purified by FCC
- washeluting with CX-ER 19:1
Sources & evidence
- ORD record
- ord-998a3095efb74849aa6ae7eba3fe975c
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04853382
Reaction notes
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