Glutaric anhydride → 2-Octanoyloxy-1-(octanoyloxymethyl)ethyl hydrogen glutarate

HRID 279909

반응식

HRID 279909 반응식
[C:1]([O:10][CH2:11][CH:12]([OH:24])[CH2:13][O:14][C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N(CC)CC)C.[C:32]1(=[O:39])[O:38][C:36](=[O:37])[CH2:35][CH2:34][CH2:33]1.C([O-])(=O)CCCCCCC>CCOCC.C(Cl)Cl>[C:32]([O:24][CH:12]([CH2:13][O:14][C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:11][O:10][C:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])(=[O:39])[CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37]

참가 물질

7

반응물 4

HCID 7940Glutaric anhydride2회HCID 8471Triethylamine2회HCID 119389OctanoateHCID 1509111,3-Dioctanoyl glycerol

생성물 1

HCID 233228862-Octanoyloxy-1-(octanoyloxymethyl)ethyl hydrogen glutarate

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

A solution of 2-hydroxy-3-octanoyloxypropyl octanoate (5.0 g.) in ether (30 ml.) was stirred with triethylamine (2.04 ml.) and glutaric anhydride (1.66 g.) for 3.5 hours. Further glutaric anhydride (0.8 g.) was then added together with triethylamine (1.0 ml.). This mixture was heated under reflux until no further starting octanoate could be detected by thin layer chromatography (silica: methylene chloride). The cooled reaction mixture was washed with 1M hydrochloric acid (2×20 ml.), then with water (2×20 ml.), dried (MgSO4) and evaporated to give 2-octanoyloxy-1-(octanoyloxymethyl)ethyl hydrogen glutarate as an oil (6.62 g.); NMR (CDCl3): 0.9 (6H, t, CH3), 1.1-2.1 (22H, m, CH2), 2.4 (8H, m, CH2CO), 4.0-4.4 (4H,m, CH2O), 5.1-5.4 (1H, br.t, CHO), 9.6 (1H, br.s, CO2H)ppm. Mass spectrum (major diagnostic peaks based on M=458, using chemical ionisation techniques): m/e 476 (M+NH4), 360 (M +NH4 --HO2C.(CH2)3.CO2H)

후처리

  1. temperatureThis mixture was heated
  2. temperatureunder reflux until
  3. customThe cooled reaction mixture
  4. washwas washed with 1M hydrochloric acid (2×20 ml.)
  5. dry with materialwith water (2×20 ml.), dried (MgSO4)
  6. customevaporated

출처 및 근거

ORD 기록
ord-7f45509cc2254f9f8333e2ba5f1b0838
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04587262

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