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

HRID 279913
Notes
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Reaction equation

HRID 279913 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c1fa1d6fb8d2410abb28b6026d0b017f
Source dataset
uspto-grants-1986_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04587262

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes