Acetone → HCID 19425370, compound

HRID 742192Notes

Reaction equation

HRID 742192 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[CH:21]=[CH2:22].[CH3:24][C:25]([CH3:27])=O>>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:13])[C:11]=1[O:12][CH2:27][CH:25]=[CH2:24])[C:5]([O:7][CH3:8])=[O:6])[CH:21]=[CH2:22]

Participants

5

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 21629585Methyl 3-bromo-4,5-dihydroxybenzoate

Product 1

HCID 19425370HCID 19425370, compound

Procedure

Methyl 3,4-dihydroxy-5-bromobenzoate (49 g, see Chem. Abs., 89:2327 g) and K2CO3 (92 g) were placed in a flask in acetone (500 ml). Allyl bromide (49 ml) was slowly added to the mixture, which was stirred at room temperature for 5 days. After filtration, solvent was evaporated, the residue taken up in ethyl acetate, washed with water, and dried (MgSO4). Evaporation of the solvent gave methyl 3,4-diallyloxy-5-bromobenzoate (65 g): NMR (DMSO-d6) 3.86 (s, 3H); 4.67 (m, 4H); 5.20-5.53 (m, 4H); 5.95-6.19 (m, 2H); 7.54 (d, 1H); 7.73 (d, 1H).

Workup

  1. filtrationAfter filtration, solvent
  2. customwas evaporated
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-6f55dd45bddd4967bc19a67c984663d4
Source dataset
uspto-grants-1996_09
Patent number
US05554606

Reaction notes

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