Continuous flow, palladium catalysed …€flow, palladium‐catalysed alkoxycarbonylation reactions...

Continuous‐flow,palladium‐catalysedalkoxycarbonylationreactionsusingaprototypereactorinwhichitispossibletoloadgasandheatsimultaneously

MichaelA.MercadanteandNicholasE.Leadbeater

DepartmentofChemistry,UniversityofConnecticut,55NorthEaglevilleRd,Storrs,CT06269‐3060USA.Fax:+18604862981;Tel:+18604865076.E‐mail:[email protected]

ELECTRONICSUPPORTINGINFORMATION

1H‐and13C‐NMR,highandlowresolutionmassspectroscopyandIRdatafor

propyl‐4‐methylbenzoate(Table2,entry7)

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

Propyl‐4‐methylbenzoate:1,2

1HNMR(400MHz,CDCl3)δppm1.03(t,J=7.51Hz,3H)1.79(m,J=7.17Hz,2H)2.40(s,3H)4.26(t,J=6.66Hz,2H)7.23(d,J=7.85Hz,1H)7.94(d,J=8.19Hz,2H).

13CNMR(101MHz,CDCl3)δppm10.78,21.88,22.39,66.59,128.06,129.28,129.81,143.66,167.01.

MS(EI):178(M+,6%),136(71%),119(100%),91(45%),65(15%),39(4%).

HRMS(ESI+),calcdforC11H14O2[M]+:179.1072,found179.1055.

FTIR(cm‐1,neat,ATR)3039(w),2965(m),2878(w),1713(s),1613(m),1461(w),1265(vs),1174(m),1104(s),748(s).

1Preparedbyalkoxycarbonylationof4‐iodotoluenewithpropanolandalsobyesterificationof4‐methylbenzoicacidwithpropanoltoconfirmidentity.2Forboilingpointandrefractiveindexdatasee:C.C.PriceandW.J.Belanger,J.Am.Chem.Soc.,1954,76,2682;forrefractiveindexsee:R.J.Washkuhn,S.ReutrakulandJ.R.Robinson,J.Pharm.Sci.,1970,59,779.

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Continuous flow, palladium catalysed …€flow, palladium‐catalysed alkoxycarbonylation reactions...

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