Triethylamine → 3-(4-Chloro-2-hydroxyphenyl)propanoic acid

HRID 910857Notes

Reaction equation

HRID 910857 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([OH:10])[CH:3]=1.C(N(CC)CC)C.[CH3:18][C:19]1(C)[O:26]C(=O)CC(=O)[O:20]1.[OH-].[Na+]>CN(C=O)C.C(O)=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][CH2:18][C:19]([OH:26])=[O:20])=[C:4]([OH:10])[CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 5201014-Chloro-2-hydroxybenzaldehyde

Product 1

HCID 673904453-(4-Chloro-2-hydroxyphenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

The subtitle compound was prepared by using the product from step i). (3.48 g) was added to a solution of triethylamine (10 ml) and formic acid (7 ml) in DMF (30 ml) after 20 minutes. Meldrum's acid (3.22 g) was added and the mixture heated to 100 C for 4 hours. The solution was basified with 2M NaOH, extracted with ether (discarded). The aqueous layer was acidified with 2M HCl, extracted with ethyl acetate, dried and concentrated under reduced pressure to give an oil. The residue was purified by chromatography on silica eluting with diethyl ether/isohexane 1:5, yield 0.40 g.

Workup

  1. temperaturethe mixture heated to 100 C for 4 hours
  2. extractionextracted with ether (discarded)
  3. extractionextracted with ethyl acetate
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil
  7. customThe residue was purified by chromatography on silica eluting with diethyl ether/isohexane 1:5, yield 0.40 g

Sources & evidence

ORD record
ord-40b7d434de8745c08019deb28343aa4d
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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