HCID 14401625, compound → HCID 14454685, compound

HRID 2373776Notes

Reaction equation

HRID 2373776 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[C:9]([OH:15])=[C:8]([CH:16]([CH3:18])[CH3:17])[CH:7]=1.C1COCC1.O>CCCCCCC.C(OCC)(=O)C>[OH:15][C:9]1[C:8]([CH:16]([CH3:18])[CH3:17])=[CH:7][C:6]([CH2:5][CH2:4][C:3]([OH:19])=[O:2])=[CH:11][C:10]=1[CH:12]([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 14401625HCID 14401625, compoundHCID 21881883Oxolane--water (1/1)

Product 1

HCID 14454685HCID 14454685, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

A solution of 2.64 g (10 mmol) of 3-(4-hydroxy-3,5-diisopropylphenyl)propanoic acid methyl ester (cf. U.S. Pat. No. 3,642,868) and 0.84 g (20 mmol) of LiOH,H2O in 80 ml of a 1/1 mixture THF/H2O was stirred at 20° C. for 7 hours. After evaporation of THF under reduced pressure, the aqueous solution was acidified with KHSO4 (1M) and extracted twice with 50 ml EtOAc. The organic layer was decanted, washed with 20 ml brine, dried over MgSO4 and filtered. The residue of evaporation was triturated with heptane to yield a white powder (67%). Melting, point: 106-106.5° C.

Workup

  1. customAfter evaporation of THF under reduced pressure
  2. extractionextracted twice with 50 ml EtOAc
  3. customThe organic layer was decanted
  4. washwashed with 20 ml brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe residue of evaporation
  8. customwas triturated with heptane

Sources & evidence

ORD record
ord-d761e93fb48f4b8da047ba38e7948f54
Source dataset
uspto-grants-2008_12
Patent number
US07459558B2

Reaction notes

Loading…