Ethanol → HCID 10133996, compound

HRID 984956Notes

Reaction equation

HRID 984956 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12]/[CH:13]=[C:14](/[C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)\[CH3:15])=[CH:7][CH:6]=1.C(O)C>[OH-].[Na+].Cl.C(OCC)(=O)C>[O:22]([C:19]1[CH:20]=[CH:21][C:16](/[C:14](/[CH3:15])=[CH:13]/[CH2:12][O:11][C:8]2[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:29])=[O:2])=[CH:10][CH:9]=2)=[CH:17][CH:18]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 2

HCID 702EthanolHCID 10293637HCID 10293637, compound

Product 1

HCID 10133996HCID 10133996, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

(E)-{4-[3-(4-Phenoxy-phenyl)-but-2-enyloxy]-phenyl}-acetic acid methyl ester (example 20 (150 mg, 0.4 mmol) was suspended in 1N NaOH (1 mL) and ethanol (5 ml) and stirred for 24 h at room temperature. The mixture was diluted with 1N HCl (1 mL) and ethyl acetate (10 mL). The aqueous layer was separated and extracted with ethyl acetate (20 mL) The organic layers were combined, washed with brine, dried (MgSO4) and evaporated to give 116 mg (80%) of the title compound.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (20 mL) The organic layers
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-ac56982edf984db99ab5426620468567
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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