Ethanol → 1-Ethoxy-2-ethylbenzene

HRID 2064680Notes

Reaction equation

HRID 2064680 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

HCID 702EthanolHCID 69972-EthylphenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 123975301-Ethoxy-2-ethylbenzeneYield 84.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. custommixture was evaporated
  2. 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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