Hydrochloric Acid → Acetic acid, 2,2'-[1,4-phenylenebis(oxy)]bis-

HRID 1882323Notes

Reaction equation

HRID 1882323 reaction equation
C[O:2][C:3](=[O:18])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([O:16]C)=[O:15])=[CH:8][CH:7]=1.Cl>[OH-].[Na+]>[C:14]([CH2:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:18])=[O:2])=[CH:7][CH:8]=1)([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 6421174dimethyl 2,2'-[1,4-phenylenebis(oxy)]diacetate

Product 1

HCID 75251Acetic acid, 2,2'-[1,4-phenylenebis(oxy)]bis-Yield 67.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

(4-Methoxycarbonylmethoxy-phenoxy)-acetic acid methyl ester 82 (100 grams, 394 mmol) was added to 3.25 M-sodium hydroxide solution (600 mL) and heated to 70° C. for 20 hours and poured onto ice cold water (1 lit) and the pH adjusted to 1 with concentrated hydrochloric acid. Crude 83 was filtered, dried, and recrystallized from DMF by precipitating with water to give pure 83 (60 grams, 67.4%) as a white powder. M.p: 254-256.5° C. IH NMR (CDCl3+DMSO, d6) 4.44 (s, 2H, OCH2), 6.72 (s, 2H, Ar).

Workup

  1. additionpoured onto ice cold water (1 lit)
  2. filtrationCrude 83 was filtered
  3. customdried
  4. customrecrystallized from DMF
  5. customby precipitating with water

Sources & evidence

ORD record
ord-e2b902c87387414f955d1494deba9d59
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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