# Patent

## Title
Sulfamoyl-2-benzofurancarboxylic acid derivative

## Abstract

Isomerization and subsequent lithium alanate reduction of sclareolide by the method of G. Ohloff, Helv. Chim Acta, 68 (1985), 2022-29, was used to obtain a diastereoisomeric decahydro-2-hydroxy-2,5,5,8a-tetramethyl1-naphthaleneethanol (mp. 191.degree. C.). 142 g of this diol were dissolved in 2,110 g of toluene, and the solution was admixed with 120 g (3 mol) of sodium hydroxide in 120 ml of water and then with 48 g (0.15 mol) of tetrabutylammonium bromide. 101 g (0.5 mol) of p-toluenesulfonyl chloride were then added twice in the course of 1 hour, and the reaction mixture was subsequently stirred for 2 hours, and admixed with 500 ml of water and thereafter thoroughly stirred for a further 10-20 minutes. The bottom, aqueous phase was separated off and washed once with 200 ml of water, and thereafter the solvent was distilled off at 300 mbar. Recrystallization of the residue left 121.6 g of isomeric dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (formula Ib; R.sup.1, R.sup.2 =CH.sub.3), of mp. 60.degree. C. and [a].sup.20.sub.D =+7.5.degree., which corresponds to a yield of 92%.

## Background
## Claims

1. A process for preparing an alkylated dodecahydronaphtho (2,1-b) furan of the formula (I): ##STR11## wherein R.sup.1 and R.sup.2 are identical and each is hydrogen or methyl, which comprises reacting an alkylated 2-hydroxydecahydronaphthalene-1-ethanol of the formula (II): ##STR12## wherein R.sup.1 and R.sup.2 are each as defined above, with a sulfonyl chloride in the presence of a basic catalyst by performing the cyclization in the presence of a concentrated aqueous alkali metal hydroxide and a phase transfer catalyst, wherein said phase transfer catalyst is a tetraalkylammonium salt of the formula (IV): ##STR13## wherein R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are identical to or different from each other and are independently alkyl of from 1 to 22 carbon atoms or alkyl of up to 25 carbon atoms, which carbon atoms are unsubstituted or substituted by hydroxyl, carboxamide or ether groups, or each of R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are phenyl or phenyl substituted with alkyl groups of up to 20 carbon atoms, and wherein X.sup.-  is an anion of an acid; or said phase transfer catalyst is a tetraalkylphosphonium salt of the formula (V): ##STR14## wherein R.sup.4, R.sup.5, R.sup.6, R.sup.7 and X.sup.31  are as defined above for the formula (IV).

2. The process as claimed in claim 1, wherein X.sup.31  is an anion of an acid selected from the group consisting of I.sup.-, Cl.sup.-, Br.sup.-, (HSO.sub.4).sup.-, (CN).sup.-  or (BF.sub.4).sup.-.

3. The process as claimed in claim 1, wherein the phase transfer catalyst is tri-n-octylmethylphosphonium iodide.

4. The process as claimed in claim 1, wherein the phase transfer catalyst is trimethylbenzylammonium chloride or tricaprylmethylammonium chloride.

5. The process as claimed in claim 1, wherein said sulfonyl chloride has the formula (III): wherein R.sup.3 is C.sub.1 -C.sub.3 -alkyl, phenyl or phenyl which is substituted in the para position by methyl, chlorine, bromine or nitro.

6. The process as claimed in claim 1, wherein said phase transfer catalyst is used in an amount of about 0.1 to 1 mole per mole of diol.

7. The process as claimed in claim 5, wherein said phase transfer catalyst is used in an amount of about 0.3 to 0.5 mole per mole of diol.

8. The process as claimed in claim 1, wherein said alkali metal hydroxide is sodium hydroxide or potassium hydroxide and is used in an amount of about 2 to 8 moles per mole of diol.

9. The process as claimed in claim 1, wherein said sulfonyl chloride of the formula (III) is selected from the group consisting of methanesulfonyl chloride, ethanesulfonyl chloride, benzenesulfonyl chloride, p-toluenesulfonyl chloride, p-chloro- or p-bromobenzenesulfonyl chloride and p-nitrobenzenesulfonyl chloride.