Benzyl Bromide → ethyl-3,4-dibenzyloxybenzoate

HRID 1868575Notes

Reaction equation

HRID 1868575 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([OH:12])[CH:6]=1)[CH3:2].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[K+].[Br-]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[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 77547Ethyl 3,4-DihydroxybenzoateHCID 253877Potassium Bromide

Product 1

HCID 11325933ethyl-3,4-dibenzyloxybenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl-3,4-dihydroxy benzoate, 4 (27.3 g, 150 mmol), benzyl bromide (40.4 mL, 340 mmol) and potassium carbonate (41.4 g, 300 mmol) in acetone (350 mL) were reacted in a similar manner as described for 8 to afford 9. Yield 41.4 g (76%); mp 68-69° C.; MS (FAB) 363 (M++1); IR (KBr) 1889, 1707; 1H NMR (200 MHz, CDCl3) δ 7.65 (s, 1H), 7.63 (dd, J=8.7 Hz, 1.7 Hz, 1H), 7.48-7.25 (m, 10H), 6.91 (d, J=8.3 Hz, 1H), 5.19 (s, 2H), 5.18 (s, 2H), 4.31 (q, J=7.1 Hz, 2H), 1.35 (t, J=7.1 Hz, 3H).

Workup

  1. customto afford 9

Sources & evidence

ORD record
ord-a70f6c6fad8348a3995ec469245e6a31
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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