Water → Benzeneacetic acid, 4-(1-methylethoxy)-

HRID 1852088Notes

Reaction equation

HRID 1852088 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14]C)=[O:13])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[OH-].[Na+].O>CO>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 525538Methyl 2-(4-isopropoxyphenyl)acetate

Product 1

HCID 799528Benzeneacetic acid, 4-(1-methylethoxy)-Yield 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(4-isopropoxyphenyl)acetate (10 g, 48.0 mmol), and NaOH (5.76 g, 144 mmol) were heated in methanol (50 mL)/Water (50 mL) solution at reflux for 2 h. Most of the MeOH was removed under vacuum and the remaining aqueous solution was acidified with 1 N HCl. The solid that precipitated from the solution was extracted into EtOAc solution. The organic layer was collected, dried over sodium sulfate, and concentrated under vacuum to give 2-(4-isopropoxyphenyl)acetic acid (8.9 g, 95% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.22-7.16 (m, 2H), 6.88-6.83 (m, 2H), 4.53 (spt, J=6.1 Hz, 1H), 3.59 (s, 2H), 1.34 (d, J=6.0 Hz, 6H).

Workup

  1. temperatureat reflux for 2 h
  2. customMost of the MeOH was removed under vacuum
  3. customThe solid that precipitated from the solution
  4. extractionwas extracted into EtOAc solution
  5. customThe organic layer was collected
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-81b10d2244da4c8487a73cc896ebca91
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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