Water → HCID 14576787, compound

HRID 2249036Notes

Reaction equation

HRID 2249036 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>C(O)(C)C>[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10393TyrosolHCID 11430Potassium CarbonateHCID 70986(4-Bromobutoxy)benzene

Product 1

HCID 14576787HCID 14576787, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 10.31 g (45 mmol) of 4-phenoxybutylbromide, 6.22 g (45 mmol) of 2-(4-hydroxyphenyl)ethanol and 6.22 g (45 mmol) of pulverized potassium carbonate in 45 ml of isopropanol was refluxed for 24 hours. The resulting mixture was cooled, mixed with water and then extracted three times with ethyl acetate. The combined extracts were washed with water and then with saturated aqueous sodium bicarbonate. They were dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on 500 g of silica gel (Merck Si60, 0.04-0.063 mm) using methylene chloride/methanol (98:2) as eluent. The product-containing fractions were evaporated in vacuo to yield 2-[4-(Phenoxybutoxy)phenyl]ethanol in the form of 9.08 g of crystals.

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperatureThe resulting mixture was cooled
  3. extractionextracted three times with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialThey were dried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on 500 g of silica gel (Merck Si60, 0.04-0.063 mm)
  8. customThe product-containing fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-3285fbbfa14b4ce2a3574565d6a87ba0
Source dataset
uspto-grants-1991_08
Patent number
US05041638

Reaction notes

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