Ethanol → 1-Ethoxy-2-ethylbenzene
Reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])[CH3:2].[C:10]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:11]=1.C(O)C.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[CH2:10]([O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:1][CH3:2])[CH3:11]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-ethylphenol (6.9 g, 56.5 mmol), triphenylphosphine (15.7 g, 60 mmol) and ethanol (6 mL, excess) in tetrahydrofuran (100 mL) was added dropwise DIAD (12.1 g, 60 mmol). After stirring for 18 hours, mixture was evaporated and the residue was chromatographed on silica gel (heptane/ethyl acetate 9/1) to give 1-ethoxy-2-ethyl benzene (7.2 g) as a clear liquid. GC-MS shows one peak, RT=5.6 minutes. MS 150 (M+).
Workup
- custommixture was evaporated
- customthe residue was chromatographed on silica gel (heptane/ethyl acetate 9/1)
Sources & evidence
- ORD record
- ord-cb0aa8c2c8614c748af3ef6663429a30
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288425B2
Reaction notes
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