# US 4,398,044 A · Synthesis of acetyl-T-alkanes

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- Number: US 4,398,044 A
- Document ID: US4398044A
- Status: Granted
- Kind: A
- Application number: 06/366,881
- Filed: 1982-04-08
- Granted: 1983-08-09
- Earliest claimed: 1982-04-08
- Assignees: Eli Lilly and Company
- Inventors: Riaz F. Abdulla
- Web page: https://patentgrep.com/patent/US4398044A

## CPC

- C07C 255/00: Carboxylic acid nitriles (cyanogen or compounds thereof C01C3/00)
- C07C 45/673: {by change of size of the carbon skeleton}
- C07C 45/72: by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C 49/04: Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C 49/173: containing halogen
- C07C 49/303: to a six-membered ring
- C07C 51/093: by hydrolysis of —CX3 groups, X being halogen
- C07C 51/377: by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups {(C07C51/36 - C07C51/373 take precedence)}
- C07C 59/185: Saturated compounds having only one carboxyl group and containing keto groups
- C07C 59/76: containing keto groups
- C07D 237/12: Halogen atoms or nitro radicals
- C07D 237/14: Oxygen atoms
- C07D 237/22: Nitrogen and oxygen atoms
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Acetyl-tertiary-alkanes are prepared by hydrolytic decarboxylation of tertiary-alkanoylacetonitriles with hydrochloric acid.

## Claims

### Claim 1

a process for preparing an acetyl-t-alkane of the formula ##STR10## wherein R is of the formula ##STR11## R.sup.1 is C.sub.1 -C.sub.4 alkyl; R.sup.2 and R.sup.3 are independently C.sub.1 -C.sub.13 alkyl, or halo-C.sub.1 -C.sub.13 alkyl;
n is 0-4;
R.sup.4 and R.sup.5 are independently hydrogen, halo or C.sub.1 -C.sub.4 alkyl; comprising hydrolytically decarboxylating a t-alkanoylacetonitrile of the formula ##STR12## with hydrochloric acid.

### Claim 2 (depends on 1)

A process of claim 1 wherein the product is a compound wherein R is of the formula ##STR13##

### Claim 3 (depends on 2)

A process of claim 2 wherein the product is a compound wherein R.sup.2 is C.sub.1 -C.sub.4 alkyl or halo-C.sub.1 -C.sub.4 alkyl.

### Claim 4 (depends on 2)

A process of claim 2 wherein the product is a compound wherein R.sup.3 is C.sub.1 -C.sub.4 alkyl or halo-C.sub.1 -C.sub.4 alkyl.

### Claim 5 (depends on 3)

A process of claim 3 wherein the product is a compound wherein R.sup.3 is C.sub.1 -C.sub.4 alkyl or halo-C.sub.1 -C.sub.4 alkyl.

### Claim 6 (depends on 5)

A process of claim 5 wherein the product is a compound wherein R.sup.2 and R.sup.3 are both C.sub.1 -C.sub.4 alkyl.

### Claim 7 (depends on 2)

A process of claim 2 wherein the product is a compound wherein R.sup.1 is unbranched.

### Claim 8 (depends on 6)

A process of claim 6 wherein the product is a compound wherein R.sup.1 is unbranched.

### Claim 9 (depends on 8)

A process of claim 8 wherein the product is a compound wherein R.sup.2 and R.sup.3 are unbranched.

### Claim 10 (depends on 2)

A process of claim 2 wherein the product is 1-acetyl-1,1-dimethylethane.

### Claim 11 (depends on 2)

A process of claim 2 wherein the product is 1-acetyl-1-ethyl-1-methylpropane.

### Claim 12 (depends on 1)

A process of claim 1 wherein the product is a compound wherein R is of the formula ##STR14##

### Claim 13 (depends on 12)

A process of claim 12 wherein the product is a compound wherein n is 2-4.

### Claim 14 (depends on 13)

A process of claim 13 wherein R.sup.4 and R.sup.5 are both hydrogen.

### Claim 15 (depends on 12)

A process of claim 12 wherein the product is 1-acetyl-1-ethylcyclohexane.

### Claim 16 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15)

A process of any one of claims 1-15 wherein the concentration of the hydrochloric acid is from about 6 N to about 12 N.

### Claim 17 (depends on 16)

A process of claim 16 wherein the concentration of the hydrochloric acid is from about 36% to about 38% by weight.

### Claim 18 (depends on 16)

A process of claim 16 wherein the temperature is from about 80.degree. to about 110.degree..