Dimethylformamide → Ethyl 3,4-diethoxybenzoate

HRID 871260Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:15][CH3:16].[C:17]([O-])([O-])=O.[K+].[K+].CN([CH:26]=[O:27])C>>[CH2:15]([O:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:27][CH2:26][CH3:17])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:16]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6332Ethyl Bromide

HCID 11430Potassium Carbonate

HCID 77547Ethyl 3,4-Dihydroxybenzoate

Product 1

HCID 586407Ethyl 3,4-diethoxybenzoateYield 90%

Conditions

Temperature: 50 °C

Procedure

According to the procedure described in Example 6A Step 1, a mixture of ethyl 3,4-dihydroxybenzoate (5.465 g, 30 mmol), bromoethane (7.192 g, 66 mmol), and K2CO3 (9.122 g, 66 mmol) in DMF (50 mL) was heated at 50° C. for 5 hours, to afford ethyl 3,4-diethoxybenzoate as solid (6.439 g, 90%). 1H NMR (300 MHz, CDCl3) δ 7.65 (dd, 1H), 7.55 (d, 1H), 6.87 (d, 1H), 4.35 (q, 2H), 4.15 (q, 4H), 1.48 (m, 6H), 1.38 (t, 3H); LC-MS (ESI) m/z 239 (M+H)+.

Sources & evidence

ORD record: ord-97bfb136667f45dba5556515cf29e26a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969587B2

Reaction notes

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