HCID 14401625, compound → HCID 14454685, compound

HRID 1244511Notes

Reaction equation

HRID 1244511 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 LiOH2H2O 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 KHSO, (1 M) 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-8b66cf8b3f8d471e9e0738808bd1a8a5
Source dataset
uspto-grants-2006_10
Patent number
US07122535B2

Reaction notes

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