Ammonium Chloride → HCID 18518366, compound

HRID 865957Notes

Reaction equation

HRID 865957 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>[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)[CH3:1]

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-1-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 crude (contains solvent) of 6-methoxyl-1-phenyl-indan-1ol.

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-ba80ba27e53a42769a5a317077fe0c14
Source dataset
uspto-grants-1996_10
Patent number
US05569655

Reaction notes

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