Catechol → NANOVAN(TM)

HRID 2059008Notes

Reaction equation

HRID 2059008 reaction equation
C1(C(=CC=CC=1)O)O.[CH2:9]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])[C:10](=C)C.C(Cl)C(=C)C.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[OH:20][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]=1[O:13][CH2:9][CH2:10]2

Participants

6

Reactant 4

HCID 289CatecholHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 785142-[(2-methyl-2-propenyl)oxy]phenol

Product 1

HCID 22013374NANOVAN(TM)Yield 45%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

It is furthermore known (see U.S. Pat. No. 3,474,171), that pyrocatechol can be converted into methallyloxyphenol with methallyl chloride in the presence of equivalent amounts of K2CO3 and KI in acetone as the diluent if the mixture is heated under reflux for 30 hours. The yield is 45% of theory. Rearrangement and cyclization to give 7-hydroxycoumaran are carried out at 200° to 275° C. without a solvent; no yields are given for these stages. Particular disadvantages for an industrial procedure are, in the alkylation stage, the long reaction times giving a low yield and the use of an equimolar amount of potassium iodide, which is expensive and can be recovered from the salt mixture for renewed use only with high losses. Because of the highly exothermic effect, solvent-free rearrangement of methallyloxyphenol can be carried out only with a great deal of technical effort.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 30 hours

Sources & evidence

ORD record
ord-ce2f2453ba95400895d2adaa97cde517
Source dataset
uspto-grants-1982_03
Patent number
US04321204

Reaction notes

Loading…