Dimethylformamide → HCID 16749113, compound

HRID 901158Notes

Reaction equation

HRID 901158 reaction equation
[Cl:1][C:2]1[C:3](O)=[C:4]([O:11][CH3:12])[CH:5]=[C:6]([CH:10]=1)C(O)=O.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:22](=[O:25])([O-])[O-:23].[K+].[K+].C(O[CH2:32][CH3:33])(=O)C.CN([CH:37]=[O:38])C>O>[CH2:14]([O:23][C:22](=[O:25])[C:6]1[CH:5]=[C:4]([O:11][CH3:12])[C:3]([O:38][CH2:37][C:33]2[CH:32]=[CH:6][CH:10]=[CH:2][CH:3]=2)=[C:2]([Cl:1])[CH:10]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 442153-Chloro-4-hydroxy-5-methoxybenzoic acid

Product 1

HCID 16749113HCID 16749113, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-chloro-vanillic acid (4.05 g, 20 mmol), benzyl bromide (8.55 g, 50 mmol) and potassium carbonate (6.90 g, 50 mmol) in DMF (60 mL) was stirred at room temperature for 18 hours. The mixture was transferred into a separation funnel and ethyl acetate (100 mL) and water (100 mL) were added, the organic layer was separated, washed with water (2×50 mL) and brine (50 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was crystallised from dichloromethane/hexane. Yield: 7.34 g (96%) colourless needles. 1H-NMR (400 MHz, CDCl3) δ=3.92 (s, 3H, —OCH3), 5.13 (s, 2H), 5.36 (s, 2H), 7.31-7.51 (m, 10H), 7.53 (d, J=2.0 Hz, 1H), 7.73 (d, J=2.0 Hz, 1H). LRMS (FAB+): 91.0 (100), 382.1 (15, [M+H]+).

Workup

  1. customThe mixture was transferred into a separation funnel
  2. customthe organic layer was separated
  3. washwashed with water (2×50 mL) and brine (50 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallised from dichloromethane/hexane

Sources & evidence

ORD record
ord-994c099e38074516b0ac7cda60a16bcd
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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