Phenol → HCID 66647327, compound

HRID 1916823Notes

Reaction equation

HRID 1916823 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C@@H:9]1[O:11][CH2:10]1>C(O)C.C(N(CC)CC)C>[CH2:13]([O:12][CH2:8][C@H:9]([OH:11])[CH2:10][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 996PhenolHCID 159746(-)-Benzyl (R)-glycidyl ether

Product 1

HCID 66647327HCID 66647327, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of phenol (3.3 g; 35 mmol), benzyl(R)-(+)-glycidyl ether (5 g; 30.5 mmol) and triethylamine (300 μl; 2.15 mmol) in absolute ethanol (80 ml) was heated to reflux and stirred for 2 hours and then cooled to 60° C. and stirred overnight. The crude reaction mixture was concentrated under reduced pressure and the residues purified by silica gel chromatography using an eluant of hexanes and ethyl acetate (85:15 v/v) to afford 5.7 g (72.5%) of the pure product. m/z (ES) 281.1 (M+Na)+.

Workup

  1. temperatureto reflux
  2. stirringstirred overnight
  3. customThe crude reaction mixture
  4. concentrationwas concentrated under reduced pressure
  5. customthe residues purified by silica gel chromatography

Sources & evidence

ORD record
ord-9aaed9c6b15c431e96c952f3787b1dc6
Source dataset
uspto-grants-2013_12
Patent number
US08618144B2

Reaction notes

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