Hydrochloric Acid → HCID 66826537, compound

HRID 1726027Notes

Reaction equation

HRID 1726027 reaction equation
[Na].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Br[CH:11]1[CH2:16][CH2:15][O:14][C:12]1=[O:13].Cl>C(O)C>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH:11]2[CH2:16][CH2:15][O:14][C:12]2=[O:13])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78084-BromophenolHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 5360545Sodium

Product 1

HCID 66826537HCID 66826537, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (23 g, 1 mol) is added in pieces to a reactor containing ethanol (1 l). The temperature of the reaction medium is stabilised at 70° C. (exothermic) before adding a solution of 4-bromophenol (173 g, 1 mol) in ethanol (150 ml). After cooling to room temperature, α-bromo-γ-butyrolactone (83 ml, 1 mol) is added slowly. The reaction medium is stirred for ten hours and is then treated by adding 1N hydrochloric acid solution (600 ml). The aqueous phase is extracted with ethyl acetate (2×1 l) and the combined organic phases are washed with water (1 l), dried over sodium sulphate, filtered and concentrated. The residue obtained is recrystallised from isopropanol (2.2 l) to give the expected compound in the form of a white powder (80.1 g, 31%).

Workup

  1. customis stabilised at 70° C.
  2. additionis then treated
  3. extractionThe aqueous phase is extracted with ethyl acetate (2×1 l)
  4. washthe combined organic phases are washed with water (1 l)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue obtained
  9. customis recrystallised from isopropanol (2.2 l)

Sources & evidence

ORD record
ord-8ed7143d8f034e1788db97afd9a618a4
Source dataset
uspto-grants-2009_02
Patent number
US07491747B2

Reaction notes

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