Hydrochloric Acid → HCID 561872, compound

HRID 1533248Notes

Reaction equation

HRID 1533248 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>CN(C)C=O.C(OCC)C>[CH2:16]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 2794569Methyl 3-(2-hydroxyphenyl)propionate

Product 1

HCID 561872HCID 561872, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To an ice-bath cooled suspension of sodium hydride (60% dispersion in mineral oil, 0.40 g) in dimethylformamide (18 ml) were added dropwise methyl 3-(2-hydroxyphenyl)propionate (1.80 g) and benzyl bromide successively. After being stirred for 30 minutes, the mixture was poured into a mixture of diethyl ether (20 ml) and 1N hydrochloric acid solution (90 ml). The organic layer was separated and the aqueous layer was extracted by diethyl ether. The combined organic layer was washed with aqueous sodium bicarbonate solution, dried and concentrated in vacuo. The residue was purified by silica gel column chromatography [eluting with ethyl acetate n-hexane (1:1)] to provide methyl 3-(2-benzyloxyphenyl)-propionate (2.33 g).

Workup

  1. temperatureTo an ice-bath cooled
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted by diethyl ether
  4. washThe combined organic layer was washed with aqueous sodium bicarbonate solution
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography [eluting with ethyl acetate n-hexane (1:1)]

Sources & evidence

ORD record
ord-64c7dde3903842f5a564008fb7d9bbde
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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