# US 4,395,560 A · Preparation of 6a,10a-trans-hexahydrodibenzopyranones

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- Number: US 4,395,560 A
- Document ID: US4395560A
- Status: Granted
- Kind: A
- Application number: 06/381,111
- Filed: 1982-05-24
- Granted: 1983-07-26
- Earliest claimed: 1982-05-24
- Assignees: Eli Lilly and Company
- Inventors: Charles W. Ryan
- Web page: https://patentgrep.com/patent/US4395560A

## CPC

- C07D 311/80: Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Reaction of an O-methyl or O-ethyl resorcinol with a cyclohexene carbinol derivative in the presence of a catalyst affords a 6a,10a-trans-1-methoxy or 1-ethoxy-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one derivative.

## Claims

### Claim 1

A process for preparing a 6a,10a-trans compound of the formula ##STR8## wherein R is C.sub.5 -C.sub.10 alkyl, C.sub.5 -C.sub.10 alkenyl, C.sub.5 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.10 cycloalkenyl, and R.sup.1 is methyl or ethyl; comprising reacting a 5-substituted resorcinol of the formula ##STR9## with a cyclohexene carbinol compound of the formula ##STR10## wherein R.sup.2 is C.sub.1 -C.sub.4 alkoxy and R.sup.3 and R.sup.4 together are a double bond, or R.sup.4 is hydrogen and R.sup.2 and R.sup.3 together are oxo or a group of the formula ##STR11## in which R.sup.5 and R.sup.6 independently are hydrogen, methyl or ethyl, and n is 0 or 1; in the presence of a catalyst selected from boron trifluoride, boron tribromide or stannic chloride.

### Claim 2 (depends on 1)

The process of claim 1 employing a cyclohexene carbinol compound wherein R.sup.2 is C.sub.1 -C.sub.4 alkoxy and R.sup.3 and R.sup.4 together are a double bond.

### Claim 3 (depends on 2)

The process of claim 2 employing a 5-substituted resorcinol wherein R.sup.1 is methyl.

### Claim 4 (depends on 3)

The process of claim 3 employing stannic chloride as catlayst.

### Claim 5 (depends on 4)

The process of claim 4 employing a 5-substituted resorcinol wherein R is C.sub.5 -C.sub.10 alkyl.

### Claim 6 (depends on 5)

The process of claim 5 employing a 5-substituted resorcinol wherein R is 1,1-dimethylheptyl.

### Claim 7 (depends on 6)

The process of claim 6 employing a cyclohexene carbinol wherein R.sup.2 is methoxy.

### Claim 8 (depends on 1)

The process of claim 1 employing a cyclohexene carbinol of the formula ##STR12##

### Claim 9 (depends on 1)

The process of claim 1 employing a cyclohexene carbinol of the formula ##STR13##

### Claim 10 (depends on 9)

The process of claim 9 employing a cyclohexene carbinol wherein n is 0.

### Claim 11 (depends on 9)

The process of claim 9 employing a cyclohexene carbinol wherein n is 1.

### Claim 12 (depends on 1)

The process of claim 1 when carried out a temperature of about -30.degree. to about 100.degree. C.

### Claim 13 (depends on 1)

The process of claim 1 when carried out at a temperature of about -20.degree. to about 0.degree. C.

### Claim 14 (depends on 1)

The process of claim 1 when carried out in a halogenated hydrocarbon reaction solvent.

### Claim 15 (depends on 1)

The process of claim 1 when carried out in the presence of about an equimolar quantity of water.