Hydrochloric Acid → Methyl 3-allyl-4-hydroxybenzoate

HRID 1690133Notes

Reaction equation

HRID 1690133 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 to reflux at 210° C. for 18 hours. The reaction solution was added with dilute hydrochloric acid (1 mol/L) and extracted with ethyl acetate. Subsequently, the organic layer was washed with brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate) and the title compound (12.26 g, yield 64%) was obtained as a colorless powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washSubsequently, the organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified

Sources & evidence

ORD record
ord-cd79117c144a44f2ba1fedec5f3c85f2
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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