Phosphoric Acid → HCID 10707604, compound

HRID 1377750Notes

Reaction equation

HRID 1377750 reaction equation
C([O:3][C:4](=[O:22])/[C:5](/[CH3:21])=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:8]=1)C.O[Li].O.OP(O)(O)=O>O1CCOCC1.O.CCOCC>[CH:16]1([O:15][C:9]2[CH:8]=[C:7](/[CH:6]=[C:5](\[CH3:21])/[C:4]([OH:22])=[O:3])[CH:12]=[CH:11][C:10]=2[O:13][CH3:14])[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

7

Reactant 3

HCID 1004Phosphoric AcidHCID 168937Lithium hydroxide, monohydrateHCID 10685933HCID 10685933, compound

Product 1

HCID 10707604HCID 10707604, compoundYield 79.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of (E)-ethyl-3-(3-cyclopentoxy-4-methoxyphenyl)-2-methyl-prop-2-en-oate (970 mg, 3.2 mmol) in 3 mL of 1,4-dioxane was added a solution of LiOH·H2O (156 mg, 3.8 mmol) in 3 mL of H2O. The resulting mixture was heated at 80° C. for 2 hr and 45° C. for 16 hr. The resulting solution was diluted with ether and poured into 1M H3PO4. The aqueous layer was extracted with ethyl acetate (2×), washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. Silica gel chromatography (95:5, CH2Cl:methanol) provided (E)-3-(3-cyclopentoxy-4-methoxyphenyl)-2-methyl-prop-2-enoic acid as a colorless solid (700 mg, 79%). Anal. Calcd for C16H20O4 : C, 69.55; H, 7.29. Found: C, 69.39; H, 7.29.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a140a406c3cb40f793ec3f7419c4d728
Source dataset
uspto-grants-1997_09
Patent number
US05665754

Reaction notes

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