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

HRID 279909

反応式

HRID 279909 の反応式
[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]

参加物

7

反応物 4

HCID 7940Glutaric anhydride2 回HCID 8471Triethylamine2 回HCID 119389OctanoateHCID 1509111,3-Dioctanoyl glycerol

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-7f45509cc2254f9f8333e2ba5f1b0838
出典データセット
uspto-grants-1986_05
特許番号
US04587262

関連ノート

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