O-Cresol → HCID 1532260, compound

HRID 1744415Notes

Reaction equation

HRID 1744415 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[C:5](Br)([CH3:7])[CH3:6])[CH3:2].[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:9])[C:5]([CH3:7])([O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH3:10])[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 335O-CresolHCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

Product 1

HCID 1532260HCID 1532260, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-bromo-2-methylpropionic acid ethyl ester (8.27 mL, 64.0 mmol) and 2-methylphenol (7.60 g, 70.2 mmol) in dioxane (100 mL) was added Cs2CO3 (31.3 g, 96.0 mmol). After the mixture was refluxed at 100° C. for 4 hours and allowed to cool down to room temperature, the solvent was evaporated under reduced pressure. The residue was dissolved in Et2O, washed with 1 N NaOH, dried, and concentrated to give 9.69 g (68%) of D1a; 1H NMR (300 MHz, CDCl3) δ 7.13 (d, J=7.3 Hz, 1 H), 7.03 (t, J=7.6 Hz, 1 H), 6.87 (t, J=7.3 Hz, 1 H), 6.66 (d, J=8.2 Hz, 1 H), 4.24 (q, J=7.1 Hz, 2 H), 2.23 (s, 3 H), 1.59 (s, 6 H), 1.25 (t, J=7.1 Hz).

Workup

  1. temperatureto cool down to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in Et2O
  4. washwashed with 1 N NaOH
  5. customdried
  6. concentrationconcentrated
  7. customto give 9.69 g (68%) of D1a

Sources & evidence

ORD record
ord-34fae2341c8c42f1a3633de0ab109b35
Source dataset
uspto-grants-2006_03
Patent number
US07015329B2

Reaction notes

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