Hydrochloric Acid → Ethyl 2-chloro-3-[4-(2-methylchroman-2-ylmethoxy)phenyl]propionate

HRID 2351515Notes

Reaction equation

HRID 2351515 reaction equation
[ClH:1].N[C:3]1[CH:21]=[CH:20][C:6]([O:7][CH2:8][C:9]2([CH3:19])[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[O:10]2)=[CH:5][CH:4]=1.N([O-])=O.[Na+].[C:26]([O:30][CH2:31][CH3:32])(=[O:29])[CH:27]=[CH2:28]>CC(C)=O.O>[Cl:1][CH:27]([CH2:28][C:3]1[CH:21]=[CH:20][C:6]([O:7][CH2:8][C:9]2([CH3:19])[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[O:10]2)=[CH:5][CH:4]=1)[C:26]([O:30][CH2:31][CH3:32])=[O:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 156139132-(4-Aminophenoxymethyl)-2-methylchromanHCID 23668193Sodium Nitrite

Product 1

HCID 15613914Ethyl 2-chloro-3-[4-(2-methylchroman-2-ylmethoxy)phenyl]propionate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

0.7 ml of concentrated aqueous hydrochloric acid was dropped, whilst ice-cooling, into a solution of 500 mg of 2-(4-aminophenoxymethyl)-2-methylchroman (prepared as described in Preparation 4) in 5 ml of acetone, and then a solution of 170 mg of sodium nitrite in 2 ml of water was added dropwise to the resulting mixture. When the dropwise additon was complete, 2 ml of ethyl acrylate were added, and the reaction mixture was heated to 40° C. 10 mg of cuprous oxide were then added gradually, and the mixture was stirred for 30 minutes. At the end of this time, the acetone was distilled off under reduced pressure, and the residue was extracted with benzene. The benzene extract was dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was subjected of silica gel column chromatography eluted with a 10:1 dy volume mixture of hexane and ethyl acetate, to afford 350 mg of the title compound as a pale yellow oily substance.

Workup

  1. distillationAt the end of this time, the acetone was distilled off under reduced pressure
  2. extractionthe residue was extracted with benzene
  3. extractionThe benzene extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure
  6. washeluted with a 10:1 dy volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-53991555ef984a70a798818fa1227b31
Source dataset
uspto-grants-1989_10
Patent number
US04873255

Reaction notes

Loading…