Bromide ion → HCID 22460221, compound

HRID 1937274Notes

Reaction equation

HRID 1937274 reaction equation
BrBr.[OH-:3].[Na+].[C:5]([C:8]1[CH:9]=[C:10]([CH:15]2[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]2)[CH:11]=[CH:12][C:13]=1[OH:14])(=[O:7])C.[Br-].Cl>O.O1CCOCC1>[OH:14][C:13]1[CH:12]=[CH:11][C:10]([CH:15]2[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]2)=[CH:9][C:8]=1[C:5]([OH:7])=[O:3]

Participants

8

Reactant 5

HCID 259Bromide ionHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 22460220HCID 22460220, compound

Product 1

HCID 22460221HCID 22460221, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

43.15 g (270 mmols) of bromine was added dropwise to a solution of 39.60 g (990 mmols) NaOH in 194 ml of water over a period of 30 minutes at 0-5° C., and stirred for a further hour at this temperature. 20.91 g (90 mmols) of 4-(3-acetyl-4-hydroxyphenyl)-cyclohexanone was dissolved at 70° C. in 100 ml of dioxane, allowed to cool to room temperature, and the emulsion formed was then added to alkali bromide solution. The reaction mixture was stirred for 3 hours at 40° C., and then over night at room temperature. 52 ml 37% HCl was added dropwise with slight cooling and the mixture was stirred for a further hour at room temperature. The precipitate was filtered off and washed with water. Recrystallisation from acetic ester gave 2-hydroxy-5-(4-oxocyclohexyl)benzoic acid.

Workup

  1. customthe emulsion formed
  2. stirringThe reaction mixture was stirred for 3 hours at 40° C.
  3. waitover night at room temperature
  4. temperaturewith slight cooling
  5. stirringthe mixture was stirred for a further hour at room temperature
  6. filtrationThe precipitate was filtered off
  7. washwashed with water
  8. customRecrystallisation from acetic ester

Sources & evidence

ORD record
ord-adb5a1c41cc84ebfa3404347ee606e73
Source dataset
uspto-grants-2002_05
Patent number
US06395351B1

Reaction notes

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