Water → HCID 10755134, compound

HRID 1264559Notes

Reaction equation

HRID 1264559 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[OH-].[K+].Cl.Cl[CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1.O>C(O)C>[N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]=[CH:25][C:16]=1[CH2:15][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10393TyrosolHCID 14797Potassium HydroxideHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 10755134HCID 10755134, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-Hydroxybenzeneethanol (103.5 g) was stirred in ethanol (1.5 l), at room temperature. A solution of potassium hydroxide (84 g) in ethanol (1.5 l) was added dropwise, over a 1 hour period. 2-(Chloromethyl)quinoline monohydrochloride was added portionwise over a 25-minutes period. The reaction mixture was stirred and refluxed for 12 hours. The reaction mixture was poured out into water (5 l) and this mixture was stirred vigorously. The precipitate was filtered off, and washed with water (2 l). Toluene was added and azeotroped on the rotary evaporator. The residue was dried, yielding 187 g (89%) of 4-(2-quinolinylmethoxy)benzeneethanol (intermediate 1, mp. 144.8° C.).

Workup

  1. temperaturerefluxed for 12 hours
  2. stirringthis mixture was stirred vigorously
  3. filtrationThe precipitate was filtered off
  4. washwashed with water (2 l)
  5. additionToluene was added
  6. customazeotroped on the rotary evaporator
  7. customThe residue was dried

Sources & evidence

ORD record
ord-bed97194c39b48d0b5bb376f3a5563ee
Source dataset
uspto-grants-2003_04
Patent number
US06544979B1

Reaction notes

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