Water → 7-Chloro-3,3-dimethyl-2,3-dihydro-1H-inden-5-ol

HRID 2419772Notes

Reaction equation

HRID 2419772 reaction equation
[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].[Cl:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1.P(=O)(O)(O)O.O>ClC1C=CC=CC=1Cl.C1C2NC3C(=CC=CC=3)SC=2C=CC=1>[Cl:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[C:11]2[C:12]=1[CH2:1][CH2:2][C:3]2([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 1004Phosphoric AcidHCID 6557IsopreneHCID 79333-Chlorophenol

Product 1

HCID 30175517-Chloro-3,3-dimethyl-2,3-dihydro-1H-inden-5-olYield 16.4%

Reagents, catalysts & solvents 2

HCID 7108PhenothiazineCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

449 g of isoprene, stabilized with 1.35 g of phenothiazine, were added dropwise over the course of 5.5 hours to a solution of 771 g of m-chlorophenol, 77 g of 85% strength phosphoric acid and 6 ml of water in 1.44 liters of o-dichlorobenzene at 150° C. To complete the reaction, stirring was continued overnight at 150° C. After cooling, the acid phase was separated off and extracted by shaking with toluene. The combined organic phases were washed until neutral. Fractional distillation gives 194 g of 7-chloro-3,3-dimethyl-5-hydroxy-indane; boiling point 105°-110° C/0.5 mm Hg; melting point 86.5° - 87.5° C. ##STR38##

Workup

  1. customthe reaction
  2. temperatureAfter cooling
  3. customthe acid phase was separated off
  4. extractionextracted
  5. stirringby shaking with toluene
  6. washThe combined organic phases were washed until neutral
  7. distillationFractional distillation

Sources & evidence

ORD record
ord-049ecd6e8eff416991056ebddebe3169
Source dataset
uspto-grants-1978_08
Patent number
US04107324

Reaction notes

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