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Natural Science Forum / Chemistry / Organic Synthesis / September 2004isopropyl phenylacetate synthesis
I was wondering how to prepare (in a lab) isopropyl phenylacetate... preferably with the acid chlroide (and also how to make that acid chloride). Thanks.  SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA > I was wondering how to prepare (in a lab) isopropyl phenylacetate... > preferably with the acid chlroide (and also how to make that acid > chloride). Thanks. Phenylacetic acid in an excess of thionyl chloride. Stir, warm, then reflux, venting SO2 and HCl. Rotovap off xs thionyl chloride. Dissolve in absolute ether with exclusion of moisture. Cool and stir. Slowly add an equivalent each of anhydrous isopropanol and pyridine together. Filter off py.HCl. Work up, dry, vacuum distill. Why not phenylacetic acid and xs. isopropanol plus a mole-% or three of tosic acid in a Soxhlet boiler, with an xs of activated 3A or 4A molecular sieves in the thimble? That gives you no waste stream for a large scale synthesis. Rotovap off the xs isopropanol and vacuum distill the product. Everything recycles except the trace of catalyst. SignatureUncle Al http://www.mazepath.com/uncleal/ (Toxic URL! Unsafe for children and most mammals) http://www.mazepath.com/uncleal/qz.pdf -- Paul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA Uncle Al wrote: > "kez.aus" wrote: >> I was wondering how to prepare (in a lab) isopropyl phenylacetate... >> preferably with the acid chlroide (and also how to make that acid >> chloride). Thanks. > Phenylacetic acid in an excess of thionyl chloride. Stir, warm, then > reflux, venting SO2 and HCl. Rotovap off xs thionyl chloride. > Dissolve in absolute ether with exclusion of moisture. Cool and > stir. Slowly add an equivalent each of anhydrous isopropanol and > pyridine together. Filter off py.HCl. Work up, dry, vacuum distill. > Why not phenylacetic acid and xs. isopropanol plus a mole-% or three > of tosic acid in a Soxhlet boiler, with an xs of activated 3A or 4A > molecular sieves in the thimble? That gives you no waste stream for a > large scale synthesis. Rotovap off the xs isopropanol and vacuum > distill the product. Everything recycles except the trace of > catalyst. Or do the first idea in one pot - phenylacetic acid + isopropanol and slowly add one mole thionyl chloride. BTW, for the first prep I would always add a catalytic amount of DMF - they don't always go without it (and if you try it without and realize its not going, it's not a good idea to add it later..... Been there, done that.... WhoooOOOSSSSSSHHHH! SignatureRon Jones Don't repeat history, see unreported near misses in chemical lab/plant at http://www.crhf.org.uk -- Paul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA Ron Jones wrote: > Uncle Al wrote: > > "kez.aus" wrote: > >> I was wondering how to prepare (in a lab) isopropyl phenylacetate... > >> preferably with the acid chlroide (and also how to make that acid > >> chloride). Thanks. > > Phenylacetic acid in an excess of thionyl chloride. Stir, warm, then > > reflux, venting SO2 and HCl. Rotovap off xs thionyl chloride. > > Dissolve in absolute ether with exclusion of moisture. Cool and > > stir. Slowly add an equivalent each of anhydrous isopropanol and > > pyridine together. Filter off py.HCl. Work up, dry, vacuum distill. > > Why not phenylacetic acid and xs. isopropanol plus a mole-% or three > > of tosic acid in a Soxhlet boiler, with an xs of activated 3A or 4A > > molecular sieves in the thimble? That gives you no waste stream for a > > large scale synthesis. Rotovap off the xs isopropanol and vacuum > > distill the product. Everything recycles except the trace of > > catalyst. > Or do the first idea in one pot - phenylacetic acid + isopropanol and slowly > add one mole thionyl chloride. BTW, for the first prep I would always add a > catalytic amount of DMF - they don't always go without it (and if you try it > without and realize its not going, it's not a good idea to add it later..... > Been there, done that.... WhoooOOOSSSSSSHHHH! Thionyl chloride reacts with i-PrOH. SignatureUncle Al http://www.mazepath.com/uncleal/ (Toxic URL! Unsafe for children and most mammals) http://www.mazepath.com/uncleal/qz.pdf -- Paul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA |
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