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

HRID 370406Notes

Reaction equation

HRID 370406 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, δ 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 (176.6 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, δ 2.48 (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-5871a6b543174369b2b698329d6e72b0
Source dataset
uspto-grants-1985_07
Patent number
US04526719

Reaction notes

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