GB820095A - Beta-alkoxycarbonyl compounds and process for manufacture of same - Google Patents
Beta-alkoxycarbonyl compounds and process for manufacture of sameInfo
- Publication number
- GB820095A GB820095A GB24077/57A GB2407757A GB820095A GB 820095 A GB820095 A GB 820095A GB 24077/57 A GB24077/57 A GB 24077/57A GB 2407757 A GB2407757 A GB 2407757A GB 820095 A GB820095 A GB 820095A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethoxy
- acid
- hexenol
- ethyl
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Abstract
Solid polyvinyl chloride resins may be plasticized with phthalic acid esters of alcohols of formula <FORM:0820095/IV (a)/1> where R1, R2 and R3 are hydrogen or C1-4 alkyl, R4 is C1-8 alkyl, and R5 is an alkyl or cycloalkyl radical having 2-10 carbon atoms, or a hydrogenated aryl or furyl group.ALSO:The invention comprises compounds of the formula <FORM:0820095/IV (a)/1> where R1, R2 and R3 are hydrogen atoms or an alkyl group containing 1-4 carbon atoms, R4 is an alkyl group containing 1-8 carbon atoms, and R5 is an aryl, furyl, alkenyl, cycloalkenyl, alkadienyl or cycloalkadienyl radical containing a gamma-delta double bond, said alkenyl radical having 2-10 carbon atoms and said alkadienyl, cycloalkadienyl and cycloalkenyl radicals having 5-10 carbon atoms. These compounds may be prepared by reacting no more than one mol. of a compound <FORM:0820095/IV (a)/2> with at least one mol. of a compound R5CHO under substantially anhydrous conditions in the presence of a Friedel-Crafts metallic halide catalyst (including BF3), sulphoacetic acid, concentrated sulphuric acid, or a catalyst composed of a boron compound containing a B-O linkage and oxalic acid, an o-hydroxy aromatic acid, or an alpha-hydroxy acid. This last catalyst may be prepared in situ or separate from the reactants, by grinding the organic carboxylic acid with the oxy-boron compound, or by adding the ingredients simultaneously to the aldehyde reactant. Specified ingredients are pyro-, meta- and ortho-boric acids and trimethyl, triethyl and tributyl borate on the one hand, and oxalic, glycolic, lactic, malic, citric, tartronic, tartaric, mucic, salicylic and mandelic acids on the other, preferably in equimolar proportions. The catalyst may be used in amounts of 0.02-2% of the reactants. The preferred ratio of reactants is 2.5-5 mols. of aldehyde per mol. of ether reactant; preferred temperatures are 10-120 DEG C. Examples describe the preparation of (1)-(8) and (19)-(23) 3-ethoxy-4-hexenol; (9) 3-methoxy-4-hexenol; (10) 3 - butoxy - 4 - hexenol; (11) 3 - ethoxy-2 - ethyl - 4 - hexenol; (12) 2,2 - dimethyl - 3-methoxy - 4 - hexenol; (13) 3 - ethoxy - 2-ethyl - 4 - octenol; (14) 3 - ethoxy - 3 - phenylpropanol; (15) 3 - ethoxy - 2 - ethyl - 3-phenylpropanol; (16) 4 - ethoxy - 5 - heptene-2 - one; (17) 3 - ethoxy - 2 - ethyl - 4,6 - octadienol; and (18) 3 - ethoxy - 2 - ethyl - 3-furylpropanol. Comprehensive lists are given of suitable reactants, and many other compounds which may be prepared are specified. The compounds of the invention may be hydrogenated with Raney nickel catalyst at 50-150 DEG C. and 500-3000 p.s.i.g. to produce the corresponding saturated alcohols, which may be esterified with phthalic acid; the phthalate esters are useful as plasticizers (see Group IV (a)). Also 3-methoxy-, 3-ethoxy- and 3-butoxy-4-hexenol may be hydrolytically dealcoholated in the presence of 50 per cent acetic acid to sorbaldehyde, which can be oxidized with silver oxide to sorbic acid.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US820095XA | 1956-08-01 | 1956-08-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB820095A true GB820095A (en) | 1959-09-16 |
Family
ID=22168092
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB24077/57A Expired GB820095A (en) | 1956-08-01 | 1957-07-30 | Beta-alkoxycarbonyl compounds and process for manufacture of same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB820095A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4371708A (en) * | 1980-06-07 | 1983-02-01 | Bayer Aktiengesellschaft | 4-Substituted 3,3-dimethyl-butan-2-ones, processes for their preparation and their use as intermediate products |
US4499308A (en) * | 1983-12-05 | 1985-02-12 | The Standard Oil Company | Catalytic reaction of acrolein and methacrolein with alcohols and glycols |
-
1957
- 1957-07-30 GB GB24077/57A patent/GB820095A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4371708A (en) * | 1980-06-07 | 1983-02-01 | Bayer Aktiengesellschaft | 4-Substituted 3,3-dimethyl-butan-2-ones, processes for their preparation and their use as intermediate products |
USRE32122E (en) * | 1980-06-07 | 1986-04-22 | Bayer Aktiengesellschaft | 4-substituted 3,3-dimethyl-butan-2-ones, processes for their preparation and their use as intermediate products |
US4499308A (en) * | 1983-12-05 | 1985-02-12 | The Standard Oil Company | Catalytic reaction of acrolein and methacrolein with alcohols and glycols |
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