Potassium Carbonate → HCID 59760048, compound

HRID 1879125Notes

Reaction equation

HRID 1879125 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Br>CN(C=O)C.C(OCC)(=O)C>[Cl:18][C:19]1[CH:20]=[C:21]([CH2:22][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=2)[C:7]([O:9][CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[C:19]([Cl:18])[CH:20]=2)=[O:8])[CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 2351885-Hydroxy-2-methylbenzoic acid

Product 1

HCID 59760048HCID 59760048, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-hydroxy-2-methylbenzoic acid (1.0 g, 6.6 mmol) in DMF (50 ml) were added potassium carbonate (1.82 g, 13.14 mmol, 2.0 eq) and 3-chlorobenzyl bromide (1.72 g, 13.14 mmol, 2.0 eq). The mixture was stirred at 70° C. for 2 hours and then left stirring at room temperature overnight. The temperature was increased to 80° C. and heating continued for a further 6 hours. After cooling the mixture was diluted with ethyl acetate (200 ml) and washed with water (2×200 ml). Organic layer was separated, dried over MgSO4, filtered and evaporated to dryness to afford the title compound as a yellow oil, 2.67 g (contains 24% of monoalkylated phenol impurity). No further purification carried out. MS (ES−) m/z 399 [M−H]− (C22H1835Cl2O3). 1H-NMR (400 MHz, CDCl3) δ 2.52 (3H, s), 5.04 (2H, s), 5.29 (2H, s), 7.02 (1H, dd, J 8.4, J 2.8), 7.16 (1H, d, J 8.4), 7.29-7.34 (6H, m), 7.43 (2H, d, J 1.2), 7.54 (1H, d, J 2.8).

Workup

  1. waitleft
  2. stirringstirring at room temperature overnight
  3. temperatureThe temperature was increased to 80° C.
  4. temperatureheating
  5. waitcontinued for a further 6 hours
  6. temperatureAfter cooling the mixture
  7. washwashed with water (2×200 ml)
  8. customOrganic layer was separated
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-96e661bc021446708ba28b8eb62467f9
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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