Isopropanol → HCID 131729976, compound

HRID 2060577Notes

Reaction equation

HRID 2060577 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[Br:6][C:7]1[CH:13]=[CH:12][C:10]([OH:11])=[CH:9][C:8]=1[OH:14].[CH:15]([OH:18])([CH3:17])[CH3:16].[OH-:19].[Na+]>O>[Br:6][C:7]12[CH:17]3[O:18][CH:15]3[CH2:16][O:19][CH2:1][CH:3]3[O:5][CH:4]3[C:9](=[C:10]([CH:12]=[CH:13]1)[OH:11])[CH:8]2[OH:14]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 811054-Bromoresorcinol

Product 1

HCID 131729976HCID 131729976, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Epichlorohydrin (122.4 g, 1.32 mol), 4-bromoresorcinol (25.0 g, 0.13 mol) and Isopropyl alcohol (100 g) were added to a 500 ml three-neck flask and warmed to 75° C. A solution of 22.2 g 50 wt % sodium hydroxide in water was added dropwise to the flask over 6 hours. The flask temperature was raised to 83° C. and held for an additional 2 hours. After the reaction, the solution was filtered and solvents were evaporated. Toluene was then added to the residual mass. The solids were filtered and the toluene was again removed, giving a light-brown oil. Further purification was conducted using vacuum distillation to give a clear liquid which crystallizes upon standing. 1H NMR (CDCl3): δppm 2.6-2.9 (4H), 3.3 (2H), 3.8-4.3 (4H), 6.3-7.4 (3H).

Workup

  1. temperatureThe flask temperature was raised to 83° C.
  2. customAfter the reaction
  3. filtrationthe solution was filtered
  4. customsolvents were evaporated
  5. additionToluene was then added to the residual mass
  6. filtrationThe solids were filtered
  7. customthe toluene was again removed
  8. customgiving a light-brown oil
  9. customFurther purification
  10. distillationvacuum distillation
  11. customto give a clear liquid which
  12. customcrystallizes

Sources & evidence

ORD record
ord-bf845a786b6d4fa29e49dd2760fa7ede
Source dataset
uspto-grants-2012_10
Patent number
US08278401B2

Reaction notes

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