Chloroacetic Acid → {4-[(1,3-Dithian-2-ylidene)(phenyl)methyl]phenoxy}acetic acid

HRID 620074Notes

Reaction equation

HRID 620074 reaction equation
[OH-].[Na+].[S:3]1[CH2:8][CH2:7][CH2:6][S:5][C:4]1=[C:9]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl[CH2:24][C:25]([OH:27])=[O:26].Cl>O>[C:25]([CH2:24][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:9](=[C:4]2[S:5][CH2:6][CH2:7][CH2:8][S:3]2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:21][CH:20]=1)([OH:27])=[O:26]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 133020044-[(1,3-Dithian-2-ylidene)(phenyl)methyl]phenol

Product 1

HCID 13302026{4-[(1,3-Dithian-2-ylidene)(phenyl)methyl]phenoxy}acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of sodium hydroxide (1.3 g) in water (30 ml), (1,3-dithian-2-ylidene)-(4-hydroxyphenyl)-phenylmethane (3.0 g) and chloroacetic acid (1.4 g) are added. The mixture is refluxed for 3 hours. The water is slowly acidified with concentrated hydrochloric acid to pH 3. The aqueous phase is extracted with water (3×20 ml). The combined organic phases are washed with water (2×10 ml) and dried over magnesium sulphate. The solvent is evaporated in vacuo. The residue is purified by column chromatography on silicagel using dichloromethane/formic acid (99:1) as eluant. The fractions containing the pure product are washed with water to neutrality, dried over magnesium sulphate and evaporated. The residue is dried in vacuo to constant weight to give (4-carboxymethoxyphenyl)-(1,3-dithian-2-ylidene)-phenylmethane, m.p. 176°-177°.

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. extractionThe aqueous phase is extracted with water (3×20 ml)
  3. washThe combined organic phases are washed with water (2×10 ml)
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent is evaporated in vacuo
  6. customThe residue is purified by column chromatography on silicagel
  7. additionThe fractions containing the pure product
  8. washare washed with water to neutrality
  9. dry with materialdried over magnesium sulphate
  10. customevaporated
  11. customThe residue is dried in vacuo to constant weight

Sources & evidence

ORD record
ord-1e57c26a61eb45d8b28e0bca0c21119c
Source dataset
uspto-grants-1989_04
Patent number
US04818765

Reaction notes

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