Water → HCID 22220878, compound

HRID 1034034Notes

Reaction equation

HRID 1034034 reaction equation
[Cl:1][CH2:2][C:3]([CH3:17])=[CH:4][CH2:5][C:6]1[C:11]([CH3:12])=[C:10]([OH:13])[C:9]([CH3:14])=[C:8]([CH3:15])[C:7]=1[OH:16].FC(F)(F)S(O)(=O)=O.O>C(Cl)(Cl)(Cl)Cl>[Cl:1][CH2:2][C:3]1([CH3:17])[CH2:4][CH2:5][C:6]2[C:7](=[C:8]([CH3:15])[C:9]([CH3:14])=[C:10]([OH:13])[C:11]=2[CH3:12])[O:16]1

Participants

5

Reactant 3

HCID 962WaterHCID 62406Trifluoromethanesulfonic acidHCID 54411420HCID 54411420, compound

Product 1

HCID 22220878HCID 22220878, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-(1-Chloro-2-methylbut-2-en-4-yl)-1,4-dihydroxy-3,5,6-trimethylbenzene (4.2 g, 16 mol) was suspended in carbon tetrachloride (200 ml). Trifluoromethanesulfonic acid (1.44 ml, 2.44 g, 16 mmol) was then added and the reaction mixture was stirred. After 30 min., water (100 ml) was added and the mixture was extracted with methylene chloride (100 ml). The organic phase was dried (MgSO4) and concentrated. This gave crude 2-chloromethyl-6-hydroxy-2,5,7,8-tetramethylchroman (5.3 g). Recrystallization from hexane (40 ml) gave 2.7 g (64 percent) of pure 2-chloromethyl-6-hydroxy-2,5,7,8-tetramethylchroman. The melting point of the product was 77° to 82° C. Other data regarding the product was:

Workup

  1. extractionthe mixture was extracted with methylene chloride (100 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated
  4. customThis gave crude 2-chloromethyl-6-hydroxy-2,5,7,8-tetramethylchroman (5.3 g)
  5. customRecrystallization from hexane (40 ml)

Sources & evidence

ORD record
ord-4c61c368ea604fa792e39562f816a92a
Source dataset
uspto-grants-1994_05
Patent number
US05313007

Reaction notes

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