Toluene → 2-Methylbenzyl alcohol

HRID 2259242Notes

Reaction equation

HRID 2259242 reaction equation
[CH3:1][O-:2].[Na+].[C:4]1([CH3:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>>[C:4]1([CH3:10])[C:9]([CH2:1][OH:2])=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 1140TolueneHCID 10942334Sodium Methoxide

Product 1

HCID 69942-Methylbenzyl alcohol

Procedure

The preferred conditions are to dissolve 1 mole of alcohol (II) and 1.25 to 1.75 mole of ester (V) in which R4 is methyl in 25 to 35 parts by weight of toluene, referred to the quantity of (II) used. The solution is heated to 65°-75° C., 0.025 to 0.05 mole of sodium methylate is added, and the toluene-methanol azeotrope formed is distilled slowly for 1 to 2 hours. A further 0.0125 to 0.025 mole of sodium methylate is added and the solution is distilled for 30 minutes to 1 hour; this last operation is repeated once more. The products of the reaction are then isolated and purified by the aforesaid techniques.

Workup

  1. temperatureThe solution is heated to 65°-75° C.

Sources & evidence

ORD record
ord-c04b6bf1b54e4cb6a258dcbae7592e6e
Source dataset
uspto-grants-1995_12
Patent number
US05472970

Reaction notes

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