Hydrochloric Acid → HCID 178490745, compound

HRID 1464004Notes

Reaction equation

HRID 1464004 reaction equation
[Br:1]C1C=C(OC)C=CC=1.[Mg:10].[O:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)C(=O)C[CH2:12]1.Cl>O1CCCC1.O>[CH3:12][O:11][C:20]1[CH:15]=[C:16]([Mg:10][Br:1])[CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 169713-BromoanisoleHCID 68110ChromanoneHCID 5462224Magnesium

Product 1

HCID 178490745HCID 178490745, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 3-methoxyphenyl magnesium bromide was prepared by adding 27.7 g of m-bromoanisole to a suspension of magnesium turnings (3.6 g) in 150 ml of tetrahydrofuran (THF) dropwise over 1 hr. The mixture was heated at reflux for 2 hrs. The resulting solution was cooled to 5° C. and a solution of 4-chromanone (20.0 g) in 50 ml of dry THF added over 2 hrs. at 15° C. The resulting mixture was stirred overnight at room temperature, cooled to 10° C., and treated with 1N HCl until pH 7 was reached. The mixture was diluted with water, extracted twice with 500 ml of ether, and the combined extracts dried over MgSO4. Filtration and evaporation gave 29.6 g of the title compound as an oil. NMR (CDCl3); δ3.81 (S,3H), 4.80 (d,J=4 Hz, 2H) 5.76 (t,J=4 Hz, 1H), 6.7- 7.4 (M,8H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hrs
  3. customat 15° C
  4. temperaturecooled to 10° C.
  5. extractionextracted twice with 500 ml of ether
  6. dry with materialthe combined extracts dried over MgSO4
  7. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-29458438176149eda841e85d1c1d3c9c
Source dataset
uspto-grants-1994_04
Patent number
US05302716

Reaction notes

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