Hydrochloric Acid → HCID 12870924, compound

HRID 457961Notes

Reaction equation

HRID 457961 reaction equation
[OH:1][C:2]1[CH:11]=[C:10](O)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]([O-:16])([O-])=O.[K+].[K+].[CH2:19](Br)[CH:20]=C.Cl>CC(C)=O>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[C:9]([O:16][CH2:13][CH:19]=[CH2:20])[CH:10]=[CH:11][C:2]=1[OH:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-Dihydroxybenzoate

Product 1

HCID 12870924HCID 12870924, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 2,4-dihydroxybenzoate (8.60 g, 51.2 mmol) was dissolved in acetone (125 mL, 0.4 M) then treated with K2CO3 (27.2 g, 196.8 mmol) and allyl bromide (6.0 mL, 8.39 g, 69.3 mmol). The reaction was heated at 60° C. for 20 h then acidified to pH 1–2 with 2 N HCl and extracted with Et2O (4×). The combined extracts were washed with saturated aq NaCl (2×), dried over Na2SO4, filtered and concentrated to give 5-allyloxy-2-hydroxy-benzoic acid methyl ester as a crude yellow oil (6.11 g, 57%): 1H NMR (DMSO-d6, 300 MHz) δ 10.74 (s, 1H), 7.69 (d, J=8.4 Hz, 1H), 6.55–6.51 (m, 2H), 6.08–5.94 (m, 1H), 5.38 (dd, J1=1.8 Hz, J2=16.8 Hz, 2H), 4.61 (d, J=5.4 Hz, 2 H), 3.81 (s, 3H).

Workup

  1. extractionextracted with Et2O (4×)
  2. washThe combined extracts were washed with saturated aq NaCl (2×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-db92e4f9bfff4cb692b0c2d7e87e9de1
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

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