2,5-Dimethoxy-3,4,6-trimethylbenzaldehyde → HCID 86653771, compound

HRID 1021197Notes

Reaction equation

HRID 1021197 reaction equation
[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([O:13][CH3:14])=[C:7]([CH3:15])[C:4]=1[CH:5]=[O:6].[CH2:16]([Mg]Br)[CH:17]=[CH2:18]>C1COCC1>[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([O:13][CH3:14])=[C:7]([CH3:15])[C:4]=1[CH:5]([OH:6])[CH2:18][CH:17]=[CH2:16]

Participants

4

Reactant 2

HCID 27526052,5-Dimethoxy-3,4,6-trimethylbenzaldehydeHCID 178455850HCID 178455850, compound

Product 1

HCID 86653771HCID 86653771, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2,5-dimethoxy-3,4,6-trimethylbenzaldehyde (6.34 g) in 125 mL THF was cooled to 0° C. and treated with 34 mL 1.0 M allyl magnesium bromide (1.0 M in THF, 1.1 equiv.) slowly over 0.25 h via dropping funnel. The solution was stirred for and additional 0.25 h and quenched by the addition of 40 mL 1.0 M aqueous citric acid and stirring until the layers clarified. The layers were separated and the aqueous layer extracted 3×50 mL EtOAc. The combined organics were washed 2×25 mL saturated aqueous NaCl, dried over Na2SO4 and concentrated to yield 9.8 g of 1-(2,5-dimethoxy-3,4,6-trimethylphenyl)but-3-en-1-ol as a brown oil. M+−H2O=233.4 m/z; 1H NMR (400 MHz, CDCl3) δ=5.90 (m, 1 H), 5.15 (m, 1 H), 5.10 (m, 1 H), 4.98 (m, 1 H), 3.78 (s, 3 H), 3.65 (s, 3 H), 2.66 (s, 1 H), 2.48 (s, 1 H), 2.25 (s, 3 H), 2.18 (s, 6H) ppm.

Workup

  1. customquenched by the addition of 40 mL 1.0 M aqueous citric acid
  2. stirringstirring until the layers
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted 3×50 mL EtOAc
  5. washThe combined organics were washed 2×25 mL saturated aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a34f093344424a789ebedc4e0f14b13a
Source dataset
uspto-grants-2014_05
Patent number
US08716527B2

Reaction notes

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