Methanol → 4-(Chloromethyl)phenol

HRID 1576945Notes

Reaction equation

HRID 1576945 reaction equation
ClC([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][Cl:12])=[CH:7][CH:6]=1)=O.CN(C)C=O.CO>C(#N)C>[Cl:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6228Dimethylformamide2×HCID 13434001Carbonochloridic acid, 4-(chloromethyl)phenyl ester2×

Product 1

HCID 356844-(Chloromethyl)phenol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Equimolar quantities of p-chloromethylphenyl chloroformate and dimethyl formamide were reacted at room temperature for one hour in acetonitrile (590 parts acetonitrile for every mole of dimethyl formamide or p-chloromethylphenyl chloroformate). Equimolar quantities of methanol were then added to the immonium salt mixture, and the solution was then stirred for about one half hour (with cooling) at 25°-30°C.

Workup

  1. temperature(with cooling) at 25°-30°C.

Sources & evidence

ORD record
ord-32f1a8b847864c6982794e800a3fe1a6
Source dataset
uspto-grants-1976_09
Patent number
US03983178

Reaction notes

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