Ammonium Chloride → HCID 18518366, compound

HRID 742443Notes

Reaction equation

HRID 742443 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[C:13]1([Li])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+]>CCOCC.C1CCCCC1.CCOCC>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[OH:12])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 3340366-Methoxy-1-IndanoneHCID 178506676HCID 178506676, compound2×

Product 1

HCID 18518366HCID 18518366, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21895417Cyclohexane diethyletherSolvent

Procedure

To a solution of 20 g (0.123 mol) of 6-methoxy-l-indanone in 500 mL of ether cooled to -20° C. was added 72 mL (0.129 mol) of 1.8M phenyllithium in cyclohexane/ether and the mixture was stirred at room temperature for 1 h. An additional (10 mL) phenyllithium solution was added and stirred at room temperature for 1 h. To the reaction mixture was added saturated ammonium chloride solution and the resulting mixture was extracted with ethyl acetate (3×250 mL), and the organic layer was dried over sodium sulfate and concentrated in vacuo to afford 32.3 g of crude (contains solvent) 6-methoxy-1-phenyl-indan-1-ol.

Workup

  1. stirringstirred at room temperature for 1 h
  2. extractionthe resulting mixture was extracted with ethyl acetate (3×250 mL)
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-beced07775054ed89e6c897c187d3029
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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