Isopropanol → HCID 131729975, compound

HRID 2060576Notes

Reaction equation

HRID 2060576 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:5]([OH:6])=[CH:4][C:3]=1[OH:10].[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl.[CH:16]([OH:19])([CH3:18])[CH3:17].[OH-:20].[Na+]>O>[Cl:1][C:2]12[CH:18]3[O:19][CH:16]3[CH2:17][O:20][CH2:11][CH:13]3[O:15][CH:14]3[C:4](=[C:5]([C:7]([Cl:9])=[CH:8]1)[OH:6])[CH:3]2[OH:10]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 7835EpichlorohydrinHCID 14798Sodium Hydroxide2×HCID 672994,6-Dichloro-1,3-benzenediol

Product 1

HCID 131729975HCID 131729975, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

4,6-Dichlororesorcinol (25 g, 0.14 mol), epichlorohydrin (129 g, 1.4 mol) and isopropyl alcohol (100 ml) were added to a three-neck round bottom flask equipped with a reflux condenser and a mechanic stirrer. A solution of sodium hydroxide (12 g) in water (14 g) was placed in an addition funnel. The flask contents were raised to 75° C. The sodium hydroxide solution was added over 6 hours while the reaction was held at 75° C. After the slow addition the reaction was held at 83° C. for an additional 2 hours. The material was filtered and the solvent was removed. The product was then redissolved in toluene and washed with deionized water. The product in toluene was collected after one wash and passed through a silica gel column. The product was collected by removal of the solvent. Yield 50%, mp 78° C., 1H NMR (CDCl3): δppm 2.7-2.9 (4H), 3.3 (2H), 3.9-4.3 (4H), 6.7-7.3 (2H).

Workup

  1. customequipped with a reflux condenser and a mechanic stirrer
  2. customwas held at 75° C
  3. additionAfter the slow addition the reaction
  4. filtrationThe material was filtered
  5. customthe solvent was removed
  6. dissolutionThe product was then redissolved in toluene
  7. washwashed with deionized water
  8. customThe product in toluene was collected after one
  9. washwash
  10. customThe product was collected by removal of the solvent

Sources & evidence

ORD record
ord-b65deacb46194548a838209f16d48b7f
Source dataset
uspto-grants-2012_10
Patent number
US08278401B2

Reaction notes

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