3-Chloro-4-nitrophenol → HCID 178443568, compound

HRID 1583227Notes

Reaction equation

HRID 1583227 reaction equation
Cl[C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:35])[C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([C@H:21]3[CH2:26][CH2:25][C@H:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:23][CH2:22]3)=[O:20])=[CH:14][C:13]=2[Cl:34])=[CH:6][CH:5]=1)=[O:3].[Cl:36][C:37]1[CH:38]=[C:39]([OH:46])[CH:40]=[CH:41][C:42]=1[N+:43]([O-:45])=[O:44]>C1C=CC=CC=1.N1C=CC=CC=1>[Cl:36][C:37]1[CH:38]=[C:39]([CH:40]=[CH:41][C:42]=1[N+:43]([O-:45])=[O:44])[O:46][C:2]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11](=[O:35])[C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([C@H:21]3[CH2:22][CH2:23][C@H:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:25][CH2:26]3)=[O:20])=[CH:14][C:13]=2[Cl:34])=[CH:8][CH:9]=1)=[O:3]

Participants

5

Reactant 2

HCID 102833-Chloro-4-nitrophenolHCID 178443567HCID 178443567, compound

Product 1

HCID 178443568HCID 178443568, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Conditions

Temperature
65 °C

Procedure

The crude 2-chloro-4-[[(trans-4-heptylcyclohexyl)carbonyl]oxy]benzoic acid p-(chlorocarbonyl)phenyl ester obtained was dissolved in 70 ml of benzene and then added dropwise to a solution of 1.04 g of 3-chloro-4-nitrophenol in 50 ml of pyridine. The reaction mixture was stirred overnight at a bath temperature of 65° C., then poured into ice-cold dilute hydrochloric acid and extracted with diethyl ether. The extract was washed four times with 50 ml of 3N hydrochloric acid each time and once with 50 ml of 2N sodium carbonate solution, washed neutral with water, dried and concentrated. The crude 2-chloro-4-[[(trans-4-heptylcyclohexyl)carbonyl]oxy]benzoic acid p-[(3-chloro-4-nitrophenoxy)carbonyl]phenyl ester (3.2 g) obtained was chromatographed on silica gel with hexane/dioxan (volume ratio 3:1). The fractions which were pure according to thin-layer chromatography (1.8 g) were recrystallized twice from ethyl acetate; m.p. (C-N) 138° C., cl.p. (N-I) 237.5° C.

Workup

  1. additionpoured into ice-cold dilute hydrochloric acid
  2. extractionextracted with diethyl ether
  3. washThe extract was washed four times with 50 ml of 3N hydrochloric acid each time
  4. washonce with 50 ml of 2N sodium carbonate solution, washed neutral with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-05b9e5e4261c4efdb630c8c34a2392f3
Source dataset
uspto-grants-1985_11
Patent number
US04550981

Reaction notes

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