Ethyl Acetate → HCID 86583663, compound

HRID 1743473Notes

Reaction equation

HRID 1743473 reaction equation
C([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][O:13][CH3:14])=[CH:7][C:6]=1[C:15]1[CH2:16][C:17]([Br:23])([CH:21]=[O:22])[CH:18]=[CH:19][CH:20]=1)C.[OH-].[K+].CCOC(C)=O>CO.O.Cl>[Br:23][C:17]1([CH:21]=[O:22])[CH:18]=[CH:19][CH:20]=[C:15]([C:6]2[CH:7]=[C:8]([O:11][CH2:12][O:13][CH3:14])[CH:9]=[CH:10][C:5]=2[C:4]([OH:24])=[O:3])[CH2:16]1

Participants

7

Reactant 3

HCID 8857Ethyl Acetate2×HCID 14797Potassium Hydroxide2×HCID 86583664HCID 86583664, compound

Product 1

HCID 86583663HCID 86583663, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 3-bromo-3-formylphenyl-4-methoxymethoxybenzoic acid ethyl ester (1.4 g, 3.56 mmol) in 10 mL MeOH/20 mL H2O was added solid KOH (220 mg, 3.91 mmol). The reaction mixture was refluxed for 3 hours then additional solid KOH (23 mg, 0.42 mmol) was added and the temperature of the reaction was lowered to ca 50° C. after which point the reaction was stirred overnight. The workup of the reaction consisted of diluting with water and acidifying with 2N HCl to pH 1 then extracting with EtOAc (3×). The combined organic layers were dried over Na2SO4 then the solvent was removed in vacuo to give a beige solid. This solid was subjected to flash chromatography (50% EtOAc: 50% Hexanes to 100% EtOAc) to give the desired acid as a beige solid plus a fraction that contained starting ester and desired acid. This fraction was rechromatographed to give more acid for a total yield of 920 mg, 70.7%. 1H NMR (CDCl3+DMSO-d6) δ 2.91 (s, 3H); 4.67 (s, 2H); 5.2–6.6 (bs, 1H); 7.26 (t, J=8.18 Hz, 1H); 7.67 (d, J=8.18 Hz, 1H); 7.73 (d, J=8.18 Hz, 1H); 7.83–7.90 (m, 2H); 8.11 (d, J=1.64 Hz, 1H); 9.90 (s, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customwas lowered to ca 50° C.
  3. extractionthen extracting with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customto give a beige solid

Sources & evidence

ORD record
ord-f38a4d3664ef4c78a395ad995e6d1665
Source dataset
uspto-grants-2006_03
Patent number
US07008636B2

Reaction notes

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