Toluene → 2-(Benzyloxy) ethanol

HRID 574040Notes

Reaction equation

HRID 574040 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH2:8].C1(C)C=CC(S(O)(=O)=[O:16])=CC=1.Cl.C(N([CH2:26][CH3:27])CC)C>ClCCl>[CH2:7]([O:8][CH2:27][CH2:26][OH:16])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 11130Triethylamine hydrochlorideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 121412-(Benzyloxy) ethanolYield 835%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
105 °C

Procedure

4.34 g of a compound (II) (purity: 94.1%), 3.14 g of 2-benzyloxyethanol and 43.4 g of toluene were prepared, 0.47 g of p-toluenesulfonic acid hydrate was added thereto, and the resultant was refluxed at 105° C. for 20 hours. Then, the reaction liquid was cooled, and 3.18 g of triethylamine hydrochloride was added thereto and stirred at room temperature for 3 hours. Thereafter, 31.4 g of dichloromethane was added to the reaction liquid, followed by filtration. The filtrate was concentrated and dried, thereby obtaining 1.31 g of a compound (VII) (yield: 19.8%).

Workup

  1. customThen, the reaction liquid
  2. temperaturewas cooled
  3. filtrationfollowed by filtration
  4. concentrationThe filtrate was concentrated
  5. customdried

Sources & evidence

ORD record
ord-0555b56ace9e460897fb7131e83ddaa3
Source dataset
uspto-grants-2015_05
Patent number
US09034556B2

Reaction notes

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