Hydrochloric Acid → Acetic acid, (3-methylphenoxy)-

HRID 1459418Notes

Reaction equation

HRID 1459418 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][C:7]([O-:9])=[O:8].C1COCC1.CO.[Li+].[OH-].Cl>O.CCOC(C)=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 47451263-MethylphenoxyacetateHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 74235Acetic acid, (3-methylphenoxy)-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 11-13 (0.145 g, 0.285 mmol) in 1:1 THF/MeOH (6 mL) was treated with LiOH (0.114 g, 28.5 mmol) dissolved in 6 mL of H2O. After stirring for 1 hour at room temperature the solvents were removed, the residue dissolved in H2O/EtOAc/10% KHSO4 and the layers separted. The water layer was washed with EtOAc, the organic layers were combined, dried, and filtered to give the intermediate acid as a yellow oil. This material was dissolved in EtOAc (10 mL), cooled to -78° C., the solution saturated with HCl gas and warmed to 0° C. for 0.5 hours, then concentrated and dried under vacuum to give 11-14 as fluffy solid.

Workup

  1. customwere removed
  2. dissolutionthe residue dissolved in H2O/EtOAc/10% KHSO4
  3. washThe water layer was washed with EtOAc
  4. customdried
  5. filtrationfiltered
  6. customto give the intermediate acid as a yellow oil
  7. temperaturecooled to -78° C.
  8. concentrationconcentrated
  9. customdried under vacuum

Sources & evidence

ORD record
ord-0f4d6cf88c1c4e7484a0cee2f933aeda
Source dataset
uspto-grants-1998_12
Patent number
US05854245

Reaction notes

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