Pyridine → 5-Chloro-2-(2,4-dichlorophenoxy)phenyl 4-[2-hexadecanoyloxy-1-(hexadecanoyloxymethyl)ethoxycarbonyl]-3,3-dimethylbutyrate

HRID 279913

反応式

HRID 279913 の反応式
Cl[C:2]([CH2:4][C:5]([CH3:50])([CH3:49])[CH2:6][C:7]([O:9][CH:10]([CH2:30][O:31][C:32](=[O:48])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:11][O:12][C:13](=[O:29])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:8])=[O:3].[CH:51]1[C:56]([Cl:57])=[CH:55][C:54]([OH:58])=[C:53]([O:59][C:60]2[CH:61]=[CH:62][C:63]([Cl:67])=[CH:64][C:65]=2[Cl:66])[CH:52]=1.N1C=CC=CC=1>C(Cl)Cl>[C:32]([O:31][CH2:30][CH:10]([CH2:11][O:12][C:13](=[O:29])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[O:9][C:7]([CH2:6][C:5]([CH3:49])([CH3:50])[CH2:4][C:2]([O:58][C:54]1[CH:55]=[C:56]([Cl:57])[CH:51]=[CH:52][C:53]=1[O:59][C:60]1[CH:61]=[CH:62][C:63]([Cl:67])=[CH:64][C:65]=1[Cl:66])=[O:3])=[O:8])(=[O:48])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]

参加物

5

反応物 3

HCID 1049PyridineHCID 5564TriclosanHCID 233229012-Hexadecanoyloxy-1-(hexadecanoyloxymethyl)ethyl 4-chloroformyl-3,3-dimethylbutyrate

生成物 1

HCID 233229005-Chloro-2-(2,4-dichlorophenoxy)phenyl 4-[2-hexadecanoyloxy-1-(hexadecanoyloxymethyl)ethoxycarbonyl]-3,3-dimethylbutyrate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 2-hexadecanoyloxy-1-(hexadecanoyloxymethyl)ethyl 4-chloroformyl-3,3-dimethylbutyrate (F) (1.5 g.), triclosan (0.4 g.) and pyridine (0.17 ml.) in methylene chloride (35 ml.) was stirred at 0°-5° C. for 3 hours and then allowed to attain ambient temperature during 45 hours. The methylene chloride was evaporated and replaced by ether (50 ml.). The mixture obtained was washed successively with water (3×20 ml.), 2M hydrochloric acid (25 ml.), saturated sodium hydrogen carbonate solution (2×20 ml.) and water (2×20 ml.), and then dried (MgSO4) and evaporated. The oil obtained crystallised on treatment with ethanol to give 5-chloro-2-(2,4-dichlorophenoxy)phenyl 4-[2-hexadecanoyloxy-1-(hexadecanoyloxymethyl)ethoxycarbonyl]-3,3-dimethylbutyrate as white crystals (0.3 g.), (m.p. just below 20° C.); NMR (CDCl3): 0.7-1.0 (6H, m, CH3CH2), 1.12 (6H, s, CCH3), 1.15-1.7 (52H,m, CH2), 2.17 (4H, m, CH2CH2CO), 2.44 (2H,s, CH2CO2CH), 2.60 (2H, s, aromatic O.CO CH2), 3.9-4.4 (4H, m, CH2O), 5.1-5.4 (1H, m, CH2CO2CH), 6.9-7.5 (6H, m, aromatic H)ppm.

後処理

  1. waitto attain ambient temperature during 45 hours
  2. customThe methylene chloride was evaporated
  3. customThe mixture obtained
  4. washwas washed successively with water (3×20 ml.), 2M hydrochloric acid (25 ml.), saturated sodium hydrogen carbonate solution (2×20 ml.) and water (2×20 ml.)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe oil obtained
  8. customcrystallised on treatment with ethanol

出典と根拠

ORDレコード
ord-c1fa1d6fb8d2410abb28b6026d0b017f
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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