1-Chloro-3-methyl-2-butene → Chroman

HRID 986847Notes

Reaction equation

HRID 986847 reaction equation
CO[C:3]1[C:8]([O:9][CH:10]([CH3:12])C)=[CH:7][CH:6]=[CH:5][C:4]=1O.[Na].[CH2:15](Cl)C=C(C)C>CCOCC>[O:9]1[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:15][CH2:12][CH2:10]1

Participants

5

Reactant 3

HCID 104291-Chloro-3-methyl-2-buteneHCID 5360545SodiumHCID 20156632HCID 20156632, compound

Product 1

HCID 136319Chroman

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5.5 g (30 millimoles) of 2-methoxy-3-isopropoxy-phenol are dissolved in 30 ml of ether whereupon 2.1 g of metallic sodium are added in small portions and the mixture is heated to boiling for an hour. To the mixture 3.2 g (30 millimoles) of prenyl chloride are added dropwise and the reaction mixture is heated to boiling for 8 hours. The reaction mixture is worked up in the usual manner. Thus 4.4 g of "chromane" are obtained. This product is dissolved in 60 ml of benzene, 1.2 g of dichloro-dicyano-benzoquinone are added and the reaction mixture is purified as described in Example 3. Thus 3.7 g of the desired compound are obtained in the form of a colorless oil, yield 50%.

Workup

  1. additionare added in small portions
  2. temperaturethe mixture is heated
  3. waitto boiling for an hour
  4. temperaturethe reaction mixture is heated

Sources & evidence

ORD record
ord-0673b7a7baf24bf28af707c9d4be0f13
Source dataset
uspto-grants-1987_12
Patent number
US04716238

Reaction notes

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