Iodine → 6-Chloro-3,3-dimethyl-2,3-dihydro-1H-inden-5-ol

HRID 2419766Notes

Reaction equation

HRID 2419766 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[CH2:4][CH2:3]1.II.S(Cl)([Cl:18])(=O)=O.O>C(O)(=O)C>[Cl:18][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([CH3:12])([CH3:1])[CH2:3][CH2:4]2)=[CH:9][C:8]=1[OH:11]

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 24648Sulfuryl chlorideHCID 786603,3-Dimethylindan-5-ol

Product 1

HCID 203143906-Chloro-3,3-dimethyl-2,3-dihydro-1H-inden-5-olYield 55%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

81 g of 3,3-dimethyl-5-hydroxy-indane were dissolved in 162 g of glacial acetic acid. After adding a few grains of iodine, 68 g of sulfuryl chloride were added dropwise over the course of about 1 hour at 40°-45° C. The mixture was then warmed to 50° C for 2 hours. The reaction solution was poured into about 1.5 liters of water. The oil which separated out was taken up in chloroform and separated off. The aqueous phase was repeatedly extracted with chloroform. The combined organic phases were washed until neutral, and concentrated. Fractional distillation gave 54 g of 6-chloro-3,3-dimethyl-5-hydroxy-indane; boiling point 134°-36° C/12 mm Hg. ##STR31##

Workup

  1. additionwere added dropwise over the course of about 1 hour at 40°-45° C
  2. customThe oil which separated out
  3. customseparated off
  4. extractionThe aqueous phase was repeatedly extracted with chloroform
  5. washThe combined organic phases were washed until neutral, and
  6. concentrationconcentrated
  7. distillationFractional distillation

Sources & evidence

ORD record
ord-9973b32afaf04910b852f79e798dbb35
Source dataset
uspto-grants-1978_08
Patent number
US04107324

Reaction notes

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