Hydrochloric Acid → Methyl 3-allyl-4-hydroxybenzoate

HRID 1919748Notes

Reaction equation

HRID 1919748 reaction equation
C([O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)C=C.Cl.CN(C)[C:18]1[CH:23]=CC=C[CH:19]=1>>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][C:14]=1[CH2:23][CH:18]=[CH2:19]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 4645407Methyl 4-(allyloxy)benzoate

Product 1

HCID 939882Methyl 3-allyl-4-hydroxybenzoateYield 64%

Conditions

Temperature
210 °C

Procedure

A mixed solution of methyl 4-(2-propen-1-yl)oxybenzoate (19.17 g, 0.10 mol) and N,N-dimethylaniline (40 mL) was heated under reflux at 210° C. for 18 hours. Dilute hydrochloric acid (1 mol/L) was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 12.26 g of the title compound (yield: 64%) as a colorless powder.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThen, the organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-9f08fa0edde94a329f2e2f2c9532ff57
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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