HCID 21804317, compound → HCID 21804319, compound

HRID 2379519Notes

Reaction equation

HRID 2379519 reaction equation
[OH:1][CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]1[CH:4]=[C:5]([C:9](=[CH2:14])[C:10]([O:12]C)=[O:11])[CH:6]=[CH:7][CH:8]=1>[OH-].[Li+].O.C(#N)C.CCCCCCC>[OH:1][CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]1[CH:4]=[C:5]([C:9](=[CH2:14])[C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 1

HCID 21804317HCID 21804317, compound

Product 1

HCID 21804319HCID 21804319, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3939Lithium HydroxideSolventHCID 6342AcetonitrileSolventHCID 8900HeptaneSolvent

Procedure

A mixture of 2.40 g (8.96 mmol) of methyl 2-(3-(hydroxy-phenyl-methyl)-phenyl)-propenoate (product from Example 15a) in 1.76 g of lithium hydroxide, 16 ml of water, 18 ml of acetonitrile and 18 ml of heptane is treated overnight with intensive stirring using a mechanic stirrer. The acetonitrile/water phase is then separated and concentrated. The resulting residue is taken up in ethyl acetate and extracted with sodium hydroxide solution. The basic extract is acidified using hydrochloric acid and extracted with ethyl acetate, dried and concentrated. Yield: 1.87 g (7.36 mmol) (82.1% of theory)

Workup

  1. additionis treated overnight
  2. customThe acetonitrile/water phase is then separated
  3. concentrationconcentrated
  4. extractionextracted with sodium hydroxide solution
  5. extractionThe basic extract
  6. extractionextracted with ethyl acetate
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6fa5a30782bc4944a563f59dfe4720fc
Source dataset
uspto-grants-1994_11
Patent number
US05362907

Reaction notes

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