Water → 2-(Diethoxymethyl)benzaldehyde

HRID 1422149Notes

Reaction equation

HRID 1422149 reaction equation
[CH2:1]([O:3][CH:4]([O:12][CH2:13][CH3:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1Br)[CH3:2].C([Li])CCC.CN(C)[CH:22]=[O:23].O>C(OCC)C>[CH2:1]([O:3][CH:4]([O:12][CH2:13][CH3:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:22]=[O:23])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 34827781-Bromo-2-(diethoxymethyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 136050632-(Diethoxymethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 10.4 g of 2-bromobenzaldehyde diethyl acetal in 200 ml of dry diethyl ether at -65° C. was added 27.5 ml of a 1.6 M solution of butyllithium in hexanes. The solution was stirred at this temperature for 30 min. then slowly warmed to -40° C. when 3.4 ml of dimethylformamide was added dropwise. The reaction was warmed to room temperature then 100 ml of water was added and the organic layer was separated. The aqueous layer was extracted with two 100 ml portions of ether and the combined organic extracts were dried over sodium sulfate and evaporated to give 8.5 g of 2-formylbenzaldehyde diethylacetal as an oil; ; 1H-NMR (200 MHz, CDCl3) d 5.06 (CHOEt).

Workup

  1. additionwas added dropwise
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with two 100 ml portions of ether
  4. dry with materialthe combined organic extracts were dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-a86d4ec3e5474c2689dcd48361cc94cb
Source dataset
uspto-grants-2000_06
Patent number
US06080773

Reaction notes

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