Resorcinol → HCID 59010057, compound

HRID 2118100Notes

Reaction equation

HRID 2118100 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].Br[CH:10]([CH3:14])[C:11](O)=[O:12].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>CS(O)(=O)=O>[OH:2][C:1]1[CH:8]=[CH:7][C:6]2[C:11](=[O:12])[CH:10]([CH3:14])[O:5][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 117292-Bromopropionic acidHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 59010057HCID 59010057, compound

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of resorcinol (5.5 g, 50 mmol) in methanesulfonic acid (75 mL) was added 2-bromopropionic acid (4.7 mL, 50 mmol) and P2O5 (4.0 g, 28 mmol). The resulting mixture was stirred for 30 min at 80° C. After cooling to room temperature, the reaction mixture was poured onto ice and extracted with chloroform (2×). The combined organic extracts were washed with brine, dried with sodium sulfate, and concentrated. The orange colored crude product (˜12 g) was carefully taken up into aqueous sodium hydroxide (2N, 245 mL) at 0-5° C., and the resulting mixture was stirred at room temperature overnight. The dark brown solution was cooled to 0° C., and carefully acidified to with concentrated HCI to pH ˜3. It was then extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried with sodium sulfate, and concentrated. The crude material was purified on a silica gel column, eluting with ethyl acetate (20-75%) in hexanes. The final product was obtained as a crystalline solid upon standing at room temperature. The NMR showed a mixture of tautomers (mostly the enol form).

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe reaction mixture was poured onto ice
  3. extractionextracted with chloroform (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customwas carefully taken up into aqueous sodium hydroxide (2N, 245 mL) at 0-5° C.
  8. stirringthe resulting mixture was stirred at room temperature overnight
  9. temperatureThe dark brown solution was cooled to 0° C.
  10. extractionIt was then extracted with ethyl acetate (3×)
  11. washThe combined organic extracts were washed with brine
  12. dry with materialdried with sodium sulfate
  13. concentrationconcentrated
  14. customThe crude material was purified on a silica gel column
  15. washeluting with ethyl acetate (20-75%) in hexanes

Sources & evidence

ORD record
ord-3949534f527941e196e2f2b06b42441d
Source dataset
uspto-grants-2008_10
Patent number
US07442808B2

Reaction notes

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