Water → HCID 59205673, compound

HRID 2242518Notes

Reaction equation

HRID 2242518 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([Cl:16])[C:3]=1[OH:17].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][OH:27].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([Cl:16])[C:3]=1[O:17][CH2:25][CH2:26][OH:27]

Participants

6

Reactant 4

HCID 962WaterHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 120841702,6-Dichloro-4-benzyloxyphenol

Product 1

HCID 59205673HCID 59205673, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 15.0 grams (0.056 mole) of 2,6-dichloro-4-(phenylmethoxy)phenol (known compound) and 15.0 grams (0.109 mole) of potassium carbonate in 200 mL of DMF was cooled to 0-4° C. and 8.4 grams (0.067 mole) of 2-bromoethan-1-ol was slowly added. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature where it was stirred during an 18 hour period. After this time water was added to the reaction mixture, and the mixture was extracted with two 150 mL portions of diethyl ether. The combined extracts were dried with sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to yield 17.1 grams of residual oil. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. extractionthe mixture was extracted with two 150 mL portions of diethyl ether
  3. dry with materialThe combined extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3426acdc5a80488db87a62b8e1cec3be
Source dataset
uspto-grants-2010_03
Patent number
US07671201B2

Reaction notes

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