1,2-Dichlorobenzene → Methyl 3-allyl-4-hydroxybenzoate

HRID 257831

Reaction equation

HRID 257831 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[C:16]1[CH:21]=CC=C[C:17]=1Cl>>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][C:14]=1[CH2:21][CH:16]=[CH2:17]

Participants

3

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 4645407Methyl 4-(allyloxy)benzoate

Product 1

HCID 939882Methyl 3-allyl-4-hydroxybenzoateYield 91%

Conditions

Temperature
183 °C

Procedure

A solution of 15.05 g (78.3 mmol) of the product of Step A in 25 mL of 1,2-dichlorobenzene was magnetically stirred and refluxed (183° C.) under an argon atmosphere for 18 hours. At this point, the reaction mixture was cooled to room temperature and applied to a 6 cm diameter by 18 cm silica gel flash chromatography column and eluted with 25% ethyl acetate-hexane to separate the 1,2-dichlorobenzene, then with 40% ethyl acetate-hexane to elute the product. The product fractions were concentrated in vacuo and the residual oil was crystallized from hexane to afford 13.70 g (91%) of the title compound.

Workup

  1. temperatureAt this point, the reaction mixture was cooled to room temperature
  2. washeluted with 25% ethyl acetate-hexane
  3. customto separate the 1,2-dichlorobenzene
  4. washwith 40% ethyl acetate-hexane to elute the product
  5. concentrationThe product fractions were concentrated in vacuo
  6. customthe residual oil was crystallized from hexane

Sources & evidence

ORD record
ord-6d5945decc894a7db381087089464d5f
Source dataset
uspto-grants-1993_11
Patent number
US05264439

Linked notes

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