IP Library Granted Patent US 11,434,216
Granted Patent B2
US 11,434,216 · App. 17/231,877 · Granted Sep 6, 2022

Preparation of 3-hydroxy-3,6-dimethylhexahydrobenzofuran-2-one and derivatives thereof

Inventors: Patrick Foley (New Haven, CT); Yonghua Yang (Niantic, CT); Tania Salam (New Haven, CT)
Assignee: P2 SCIENCE, INC.
C07D307/83A23L27/2052A23L27/88A61K8/4973A61Q13/00C07C45/66A23V2002/00C07C2601/16
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Quick Facts
Patent No.
US 11,434,216
App. No.
17/231,877
Granted
Sep 6, 2022
Kind
B2
Abstract

The present invention relates to the synthesis of intermediate compounds which can be used in the synthesis of mint lactone and related compounds, including 3,6-dimethylhexahydrobenzofuran-2-ones, isomers, and other derivatives.

Claims (13)

1. A method of producing (R)-1-(4-methylcyclohex-1-en-1-yl)ethanone, having the general formula (XIX):

Comprising the steps of:

(a) providing a compound having the general formula (VI):

and

(b) dehydrating said compound, to produce the compound of Formula (XIX).

2. The method of claim 1 , wherein said dehydration is catalyzed by an acid.

3. The method of claim 2 , wherein said acid is a cationic resin.

4. The method of claim 2 , wherein said dehydration is performed continuously.

5. The method of claim 2 , wherein said dehydration is performed at an elevated temperature.

6. The method of claim 5 , wherein said temperature is between 80° C. and 140° C.

7. The method of claim 3 , wherein said acid is an Amberlyst-type cationic resin.

8. The method of claim 2 , wherein said dehydration is carried out in toluene solvent.

9. The method of claim 6 , wherein said temperature is between 110° C. and 130° C.

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Feb 6, 2023
From: HG VENTURES LLC
To: P2 SCIENCE, INC.
Reel/Frame 062650/0301 →
SECURITY INTEREST Recorded Dec 3, 2022
From: P2 SCIENCE, INC.
To: HG VENTURES LLC
Reel/Frame 062050/0152 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2021
From: FOLEY, PATRICK; YANG, YONGHUA; SALAM, TANIA
To: P2 SCIENCE, INC.
Reel/Frame 057438/0290 →
Continuity (5)
Continuation 16458981 · Jul 1, 2019
Division 15759135
Provisional Application 62259269 · Nov 24, 2015
Provisional Application 62217094 · Sep 11, 2015
Related Publication 20210230132A1 · Jul 29, 2021