Hydrochloric Acid → HCID 86637914, compound

HRID 2389365Notes

Reaction equation

HRID 2389365 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=1)[O:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl.C([O-])(O)=O.[Na+]>CCO>[OH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=1)[O:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86637915HCID 86637915, compound

Product 1

HCID 86637914HCID 86637914, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl {3-[3-(tetrahydro-2H-pyran-2-yloxy)propoxy]phenoxy}acetate (3.54 g. crude) in EtOH (34.5 mL) was added 1M HCl aqueous solution (20.4 mL) at ambient temperature. The mixture was stirred for an hour at ambient temperature. The reaction mixture was neutralized with saturated NaHCO3 aqueous solution and evaporated in vacuo. The resulting residue was dissolved in EtOAc (50 mL) and washed with brine (30 mL). The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo to give crude oil. The crude oil was purified by silica gel column chromatography (n-hexane:EtOAc=2:1-1:1) to give ethyl [3-(3-hydroxypropoxy)phenoxy]acetate (2.1 g) as a colorless oil.

Workup

  1. customevaporated in vacuo
  2. dissolutionThe resulting residue was dissolved in EtOAc (50 mL)
  3. washwashed with brine (30 mL)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give crude oil
  8. customThe crude oil was purified by silica gel column chromatography (n-hexane:EtOAc=2:1-1:1)

Sources & evidence

ORD record
ord-d02ef0fb5ee7412e9c3418a81bccd6fe
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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