Acetic Anhydride → Perilla alcohol

HRID 1604758

반응식

HRID 1604758 반응식
[CH3:1][C:2]1([CH3:11])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][C:6]12[O:10][CH2:9]1.C(OC(=O)C)(=O)C>C(O)(=O)C>[CH3:11][C:2]([C@@H:3]1[CH2:4][CH:5]=[C:6]([CH2:9][OH:10])[CH2:7][CH2:8]1)=[CH2:1]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 930462,10-Epoxypinane

생성물 1

HCID 369312Perilla alcohol

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Among other routes that have been developed to prepare perillyl alcohol from beta pinene oxide is that reported by T. K. Keenan in 1966 who produced perillyl acetate from beta-pinene oxide by refluxing beta-pinene oxide with acetic anhydride and acetic acid for seven hours followed by removal of the acetate to afford a nine percent (9%) yield of perillyl alcohol based on the starting beta-pinene oxide (B.S. Thesis Mass. Institute of Tech.). The applicants found the process to be reproducible albeit in low yield. F. C. Delay in Swiss Patent 5671/84 reported the production of perillyl alcohol in which he treated beta-pinene oxide with nitromethane and ammonium nitrite at a temperature between 20° C. and 90° C. in an overall yield of thirty percent (30%). Two years later Wang and co-workers published in Tetrahedron 1986, 620-638 complete details of this procedure and reported an overall yield of sixty-eight percent (68%) perillyl alcohol.

후처리

  1. customfollowed by removal of the acetate

출처 및 근거

ORD 기록
ord-bfd85e66572b4d889adea2b672358d80
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05994598

연결된 노트

불러오는 중…