Benzyl Chloride → HCID 12398517, compound

HRID 2277031Notes

Reaction equation

HRID 2277031 reaction equation
C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[CH2:20]([O:7][C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 24522Ethyl 3-hydroxybenzoate

Product 1

HCID 12398517HCID 12398517, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

K2CO3 (66.8 g, 0.48 mol) was added to a stirred solution of ethyl 3-hydroxybenzoate (1) (40.0 g, 0.24 mol) and (chloromethyl)benzene (33.5 g, 0.26 mol) in DMF (256 mL) and the reaction mixture was heated at 90° C. for 3 h. The reaction mixture was filtered through Celite, the filtrate was diluted with water (500 mL), extracted with EtOAc (500 mL). The organic layer was washed with brine (500 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to give ethyl 3-(benzyloxy)benzoate (2) as colorless liquid. Yield (61.0 g, 98%); 1H NMR (400 MHz, DMSO-d6) δ 7.56-7.53 (m, 2H), 7.47-7.44 (m, 3H), 7.39 (t, J=7.2 Hz, 2H), 7.35-7.29 (m, 2H), 5.17 (s, 2H), 4.30 (q, J=7.2 Hz, 2H), 1.31 (t, J=7.2 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. additionthe filtrate was diluted with water (500 mL)
  3. extractionextracted with EtOAc (500 mL)
  4. washThe organic layer was washed with brine (500 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eafcbab3af9145c4a8d86e717af0338d
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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