Dimethylformamide → 3,4-Dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzaldehyde

HRID 1382685Notes

Reaction equation

HRID 1382685 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH2:12][O:13][CH3:14])[C:6]([CH3:15])=[C:5](Br)[C:4]=1[O:17][CH2:18][O:19][CH3:20].C([Li])CCC.CN(C)[CH:28]=[O:29]>CCOCC.CCCCCC>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH2:12][O:13][CH3:14])[C:6]([CH3:15])=[C:5]([CH:28]=[O:29])[C:4]=1[O:17][CH2:18][O:19][CH3:20]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 127215421-Bromo-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzeneHCID 178418339Butyllithium

Product 1

HCID 141803203,4-Dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzaldehydeYield 80%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To a cold solution of 2,3-dimethoxy-5-methyl-1,4-bismethoxymethyloxy-6-bromobenzene (oily substance, 67 2.34 (3H), 3.57 (3H), 3.64 (3H), 3.84 (6H), 5.01 (2H), 5.09 (2H)), (9.00 g, 25.6 mmol) in absolute ether (90 ml) was added a solution of 15% n-butyllithium in hexane (17.6 ml). The mixture was stirred for 30 minutes. Dimethylformamide (9.36 g, 128 mmol) was added and the reaction was continued under the same conditions for 30 minutes. Working up in a conventional manner gave 2,3-dimethoxy-5-methyl-1,4-bismethoxymethyloxy-6-formylbenzene (oily substance,δ2.48 (3H), 3.55 (3H), 3.58 (3H), 3.85 (3H), 3.95 (3H), 4.99 (2H), 5.13 (2H)). Yield 80%.

Workup

  1. waitthe reaction was continued under the same conditions for 30 minutes

Sources & evidence

ORD record
ord-1e79448f0e984f80a4da0d0f73fcedf3
Source dataset
uspto-grants-1989_02
Patent number
US04808339

Reaction notes

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