Sodium Hydroxide → HCID 21407954, compound

HRID 2072324Notes

Reaction equation

HRID 2072324 reaction equation
C(OC(=O)CC1C=CC=CC=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH3:29])[CH2:21][CH2:20]2)=[CH:15][CH:14]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-:37].[Na+]>C1COCC1.O>[C:16]1([CH:19]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]([CH3:29])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[CH2:20][OH:37])[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54519580HCID 54519580, compound

Product 1

HCID 21407954HCID 21407954, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 10 g. of 2-[4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)-phenoxy]-phenylacetic acid ethyl ester in 25 ml. of the THF is added dropwise, over the course of 30 minutes, to a solution of 1.1 g. of LiAlH4 in 25 ml. of THF. The mixture is boiled for 3 hours, cooled, a mixture of 10 ml. of water and 40 ml. of THF and then 10 ml. of concentrated sodium hydroxide solution are added dropwise, the phases are separated and the organic phase is evaporated to give 2-phenyl-2-[4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)phenoxy)-ethanol; nD20 1.6085. Hydrochloride, softens above 75° C.

Workup

  1. temperaturecooled
  2. additiona mixture of 10 ml
  3. customthe phases are separated
  4. customthe organic phase is evaporated

Sources & evidence

ORD record
ord-3d6a3facbdbe4d6f835ad5dcc73e1cd9
Source dataset
uspto-grants-1977_09
Patent number
US04051173

Reaction notes

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