HCID 69037597, compound → HCID 69039171, compound

HRID 853166Notes

Reaction equation

HRID 853166 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[CH:9][CH:8]=1>O1CCCC1.Cl>[F:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[CH2:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH2:4][C:3]([OH:22])=[O:2])=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 69037597HCID 69037597, compound

Product 1

HCID 69039171HCID 69039171, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 500 mg of 3-[4-(3-fluoro-benzyloxy)-phenoxy]-propionic acid methyl ester in a mixture of 5 ml of tetrahydrofurane and 25 ml of hydrochloric acid (19%) was heated at 70° C. for 7 h. For the working-up, the tetrahydrofurane was evaporated under reduced pressure and the aqueous was extracted three times with 40 ml of ethyl acetate. The combined organic layers were dried over magnesium sulphate and evaporated under reduced pressure. The crude product was triturated in ether and the solid material collected on a filter funnel. After drying there were obtained 114 mg (30% of theory) of 3-[4-(3-fluoro-benzyloxy)-phenoxy]-propionic acid as white crystals.

Workup

  1. customthe tetrahydrofurane was evaporated under reduced pressure
  2. extractionthe aqueous was extracted three times with 40 ml of ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customThe crude product was triturated in ether
  6. customthe solid material collected on a filter funnel
  7. customAfter drying there

Sources & evidence

ORD record
ord-e13daed64aac4b82b8cf63924fa227cf
Source dataset
uspto-grants-2007_08
Patent number
US07253318B2

Reaction notes

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