Dimethylformamide → 2-Benzyloxy-4-(1,1-dimethylheptyl)benzaldehyde

HRID 1074508Notes

Reaction equation

HRID 1074508 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]([CH3:24])([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:17])[CH:12]=[CH:13][C:14]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].CN(C)[CH:28]=[O:29]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]([CH3:24])([CH3:17])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:12]=[CH:13][C:14]=1[CH:28]=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 5462224MagnesiumHCID 128821642-(Benzyloxy)-1-bromo-4-(2-methyloctan-2-YL)benzene

Product 1

HCID 127882872-Benzyloxy-4-(1,1-dimethylheptyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3-benzyloxy-4-bromophenyl)-2-methyloctane (100 g., 0.257 mole) in tetrahydrofuran (500 ml.) was slowly added to 70-80 mesh magnesium (12.3 g., 0.514 mole) at such a rate that reflux was maintained. Upon completion of addition, the reaction mixture was stirred until it cooled to room temperature. It was then further cooled to 0° C. Dimethylformamide (29.8 ml., 0.385 mole) was added dropwise to the reaction mixture over a 25 minute period (reaction temperature<10° C.). The reaction mixture was then allowed to warm and was stirred for 40 minutes at room temperature. The reaction mixture was quenched by addition to a saturated aqueous solution of cold ammonium chloride (1800 ml.) and the product extracted with ether (one liter). The ether extract was washed twice with saturated sodium chloride (1500 ml.), dried over magnesium sulfate and evaporated to a quantitative yield of the title compound as an oil.

Workup

  1. temperaturethat reflux
  2. temperaturewas maintained
  3. additionUpon completion of addition
  4. temperatureIt was then further cooled to 0° C
  5. custom(reaction temperature<10° C.)
  6. temperatureto warm
  7. stirringwas stirred for 40 minutes at room temperature
  8. customThe reaction mixture was quenched by addition to a saturated aqueous solution of cold ammonium chloride (1800 ml.)
  9. extractionthe product extracted with ether (one liter)
  10. extractionThe ether extract
  11. washwas washed twice with saturated sodium chloride (1500 ml.)
  12. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-19be148c95a14a04aabc706d8026cb44
Source dataset
uspto-grants-1983_07
Patent number
US04391827

Reaction notes

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