Hydrochloric Acid → HCID 18348865, compound

HRID 2268563Notes

Reaction equation

HRID 2268563 reaction equation
C([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH:14]=[O:15])[CH:8]=1)C.[OH-].[Na+].C(OCC)(=O)C.Cl>CO>[CH:14]([C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([CH3:13])[CH:10]=1)[O:6][CH2:5][C:4]([OH:16])=[O:3])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 54448675HCID 54448675, compound

Product 1

HCID 18348865HCID 18348865, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 2-(3-formyl-5-methyl-phenoxy)-acetic acid ethyl ester (0.79 g) in methanol (4 ml) at 5° C. was treated with a 2M sodium hydroxide solution (3.6 ml). After 15 min the mixture was allowed to warm to room temperature. After a further 2 h the stirred solution was again cooled to 5° C. and covered with ethyl acetate and the aqueous layer was adjusted to acidic pH with 2M hydrochloric acid. The layers were separated and the aqueous phase was extracted with more ethyl acetate. The combined organic phase was washed with water and brine and dried with magnesium sulphate. Concentration gave a gummy solid which was triturated with diethyl ether giving, after drying, the title compound (0.47 g) as a pale yellow solid. Hplc system 1 (λ=254 nm) Rt 5.2 min.

Workup

  1. temperatureAfter a further 2 h the stirred solution was again cooled to 5° C.
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with more ethyl acetate
  4. washThe combined organic phase was washed with water and brine
  5. dry with materialdried with magnesium sulphate
  6. concentrationConcentration
  7. customgave a gummy solid which
  8. customwas triturated with diethyl ether giving
  9. customafter drying

Sources & evidence

ORD record
ord-d8b2d58cdaa54f1cba8cb333ac7d4d6c
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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