Toluene → 1-(2-Methylphenyl)ethanol

HRID 620514Notes

Reaction equation

HRID 620514 reaction equation
ClC(Cl)C.[C:5]1([CH3:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Al+3].[Cl-].[Cl-].[Cl-].[CH2:16]1[O:18][CH2:17]1>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[C:5]1([CH3:11])[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:17]([OH:18])[CH3:16]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6354Ethylene OxideHCID 63651,1-DichloroethaneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1109531-(2-Methylphenyl)ethanol

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

400 g of dichloroethane and 110 g (1.2 mol) of toluene were introduced initially together with 63 g (0.47 mol) of AlCl3 in the presence of 3 g (10-2 mol) of titanium tetraisopropylate or in the absence of titanium alcoholate. 44 g (1 mol) of ethylene oxide were added in the course of 1.5 h at the temperature stated in Table 3. After hydrolysis the reaction mixture was concentrated and analyzed by gas chromatography. The yields of 2-tolylethanol, obtained as a mixture of isomers, based on converted toluene, are shown in the following table:

Workup

  1. customAfter hydrolysis the reaction mixture
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-d4fe3972e3324dd3bfde93205ca7b016
Source dataset
uspto-grants-1989_04
Patent number
US04820882

Reaction notes

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