Hydrochloric Acid → HCID 22170609, compound

HRID 2108719Notes

Reaction equation

HRID 2108719 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([O:14]C)=[O:13])[CH:8]=[CH:9][CH:10]=1.[OH-].[Na+].Cl>CO>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22170578HCID 22170578, compound

Product 1

HCID 22170609HCID 22170609, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(2-chloro-ethoxy)-phenylacetate (7.0 g, 32.9 mmol) was dissolved in methanol (40 mL) and 6N NaOH (5.5 mL) was added. The mixture was stirred at room temperature overnight then acidified by addition of 6N hydrochloric acid (5.5 mL). A white precipitate formed which was filtered, washed with 1N HCl, water and dried. 3-(3-Chloroethoxy)-phenylacetic acid (6.5 g, 99%). 1H NMR (500 MHz, CDCl3) δ3.55 (s, 2H), 3.75 (t, 2H), 4.15 (t, 2H), 6.78 (dd, 1H), 6.80 (d, 1H), 6.84 (dd, 1H), 7.16 (dd, 1H).

Workup

  1. customA white precipitate formed which
  2. filtrationwas filtered
  3. washwashed with 1N HCl, water
  4. customdried

Sources & evidence

ORD record
ord-8923d6954c774e6eb5c8ef7718ea2886
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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