Phenol → HCID 14251338, compound

HRID 1669641Notes

Reaction equation

HRID 1669641 reaction equation
[C:1]1(=O)[CH2:4][CH2:3][CH2:2]1.[C:6]1([OH:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>Cl>[C:1]1([C:9]2[CH:10]=[CH:11][C:6]([OH:12])=[CH:7][CH:8]=2)([C:9]2[CH:10]=[CH:11][C:6]([OH:12])=[CH:7][CH:8]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 996PhenolHCID 14496Cyclobutanone

Product 1

HCID 14251338HCID 14251338, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Cyclobutanone (1.2 g, 17 mmol) and phenol (4.8 g, 51 mmol) were stirred in concentrated HCl (7 mL) at 40° C. for 72 h. The resulting slurry was filtered and the filter cake was dissolved in EtOAc and washed with saturated NaHCO3 (aq) and brine. The organic layer was concentrated to give a solid which was recrystallized from EtOAc/CH2Cl2 to provide the title compound. LCMS (ESI, neg. ion): m/z=239 [M−H]−; 479 [2M−H]−. 1H NMR (500 MHz, CD3OD): δ 7.10 (d, J=8.6 Hz, 4H), 6.70 (d, J=8.6 Hz, 4H), 2.65 (t, J=7.5 Hz, 4H), 1.93 (quint, J=7.5 Hz, 2H).

Workup

  1. filtrationThe resulting slurry was filtered
  2. dissolutionthe filter cake was dissolved in EtOAc
  3. washwashed with saturated NaHCO3 (aq) and brine
  4. concentrationThe organic layer was concentrated
  5. customto give a solid which
  6. customwas recrystallized from EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-6f787a03deff4e91a6cfc925850f6f89
Source dataset
uspto-grants-2011_08
Patent number
US07989472B2

Reaction notes

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