Acetic Acid → HCID 18926072, compound

HRID 1980153Notes

Reaction equation

HRID 1980153 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:19]([C:22]2[CH:27]=[C:26]([Cl:28])[C:25]([O:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[CH:32][CH:31]=3)=[C:24]([Cl:39])[CH:23]=2)([CH3:21])[CH3:20])[CH:5]=[C:6]([Cl:18])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1.C(O)(=O)C.[OH-].[Na+].O=C1O[C@H]([C@H](CO)O)C(O)=C1O>Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:19]([C:22]2[CH:27]=[C:26]([Cl:28])[C:25]([O:29][C:30]3[CH:31]=[CH:32][C:33]([NH2:36])=[CH:34][CH:35]=3)=[C:24]([Cl:39])[CH:23]=2)([CH3:21])[CH3:20])[CH:5]=[C:6]([Cl:18])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium Hydroxide2×HCID 20437480HCID 20437480, compoundHCID 54670067L-Ascorbic Acid

Product 1

HCID 18926072HCID 18926072, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To avoid reductive dehalogenation, the 2,2-bis[3,5-dichloro-4-(4-nitrophenoxy)phenyl]propane was reduced chemically, rather than catalytically hydrogenated. To a magnetically stirred slurry in a 1-liter Erlenmeyer flask of 53.5 g (0.088 mole) of the dinitro compound and 265 mL of acetic acid warmed to 50°-60° C. there was added a solution of 131 g of (0.58 mole) stannous chloride dihydrate in 132 mL of conc. hydrochloric acid over a 10-minute period. The exothermic reduction raised the temperature to about 100° C., and external heating was stopped. After stirring 1 hr, a chilled solution of 14.0 g (0.35 mole) of sodium hydroxide in 440 mL of water containing 1.0 g of ascorbic acid (antioxidant) was added. Thereafter, every few minutes, 2 g portions of sodium hydroxide were added until an alkaline reaction with pH paper was obtained. The insoluble product, 2,2-bis[3,5-dichloro-4-(4-aminophenoxy)phenyl]propane, was isolated as a white powder by filtration, washing with water containing 0.5 wt % of ascorbic acid, and drying to a constant weight in vacuo at 60° C. Yield, 42.0 g (87%).

Workup

  1. temperatureexternal heating
  2. customwas obtained

Sources & evidence

ORD record
ord-f3c8292a799340279c17c6eab75121d6
Source dataset
uspto-grants-1984_11
Patent number
US04485140

Reaction notes

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