Water → HCID 18518366, compound

HRID 2299190Notes

Reaction equation

HRID 2299190 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][O:10][C:11]1[CH:19]=[C:18]2[C:14]([CH2:15][CH2:16][C:17]2=[O:20])=[CH:13][CH:12]=1.[NH4+].[Cl-].O>CCOCC.C1COCC1>[CH3:9][O:10][C:11]1[CH:19]=[C:18]2[C:14]([CH2:15][CH2:16][C:17]2([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[OH:20])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 3340366-Methoxy-1-IndanoneHCID 178418255HCID 178418255, compound

Product 1

HCID 18518366HCID 18518366, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.0 M phenylmagnesium bromide in Et2O (680 mL, 2.04 mole) under argon at ambient temperature was diluted with Et2O (700 mL) with stirring, and a solution of 6-methoxy-1-indanone (277 g, 1.71 mole) in THF (1400 mL) was added dropwise over 1 hr. The reaction mixture was stirred for 2 h at ambient temperature and then was poured with stirring into saturated NH4Cl (2.8 L). H2O (1.4 L) was added, and the organic phase separated. The aqueous phase was extracted with Et2O (2×1 L), and the combined organic extracts were concentrated to give crude 6-methoxy-1-phenyl-1-indanol (445 g) as a brown oil. This oil was dissolved in toluene (2.5 L), and p-toluenesulfonic acid monohydrate (12.3 g, 0.065 mole) was added. The solution was stirred and heated at reflux for 16 hr using a Dean-Stark trap with a condenser. H2O collection was minimal after 2 h and totaled 28 mL. The solution was cooled and extracted sequentially with 5% aqueous Na2CO3 (1 L) and H2O (2×1 L). The organic layer was concentrated to give a dark brown oil (400 g). This oil was distilled under vacuum to give the title compound (298.2 g, 79%) as a yellow oil: bp 152-190° C./2.0 Torr; TLC (10% EtOAc/hexanes) Rf0.75.

Workup

  1. stirringThe reaction mixture was stirred for 2 h at ambient temperature
  2. additionwas poured
  3. customthe organic phase separated
  4. extractionThe aqueous phase was extracted with Et2O (2×1 L)
  5. concentrationthe combined organic extracts were concentrated

Sources & evidence

ORD record
ord-8999c0d2cde1419dac9803798b6e55dc
Source dataset
uspto-grants-2002_12
Patent number
US06495560B1

Reaction notes

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