Benzyl Bromide → Ethyl 3,5-bis(benzyloxy)benzoate

HRID 1868570Notes

Reaction equation

HRID 1868570 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([OH:12])[CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[K+].[Br-]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([O:11][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:8]=[C:7]([O:12][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 20098Benzoic acid, 3,5-dihydroxy-, ethyl esterHCID 253877Potassium Bromide

Product 1

HCID 3016563Ethyl 3,5-bis(benzyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of ethyl-3,5-dihydroxy benzoate, 3 (16.8 g, 92 mmol) in acetone (350 mL) were added potassium carbonate (27.6 g, 200 mmol) and benzyl bromide (23.8 mL, 200 mmol) and stirred at room temperature for 9 h. Reaction mixture was filtered, concentrated on rotavapor and the crude product purified by column chromatography to afford 8. Yield 24.7 g (74%); mp 63-65° C.; MS (FAB) 363 (M++1); IR (KBr) 1824, 1708; 1H NMR (200 MHz, CDCl3) δ 7.34-7.35 (m, 10H), 7.30 (d, J=2.3 Hz, 2H), 6.79 (t, J=2.2 Hz, 1H), 5.07 (s, 4H), 4.36 (q, J=7.1 Hz, 2H), 1.38 (t, J=7.1 Hz, 3H).

Workup

  1. customReaction mixture
  2. filtrationwas filtered
  3. concentrationconcentrated on rotavapor
  4. customthe crude product purified by column chromatography
  5. customto afford 8

Sources & evidence

ORD record
ord-8fb6d35e3b9d4b3f8cecfbe4c72bff64
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

Loading…