Water → 3,3,6,7-Tetramethyl-2,3-dihydro-1H-inden-5-ol

HRID 903579Notes

Reaction equation

HRID 903579 reaction equation
[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].[CH3:6][C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=1[OH:14].P(=O)(O)(O)O.O>ClC1C=CC=CC=1Cl.C1C2NC3C(=CC=CC=3)SC=2C=CC=1>[OH:14][C:8]1[CH:9]=[C:10]2[C:11](=[C:12]([CH3:13])[C:7]=1[CH3:6])[CH2:1][CH2:2][C:3]2([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 1004Phosphoric AcidHCID 6557IsopreneHCID 106872,3-Dimethylphenol

Product 1

HCID 30179823,3,6,7-Tetramethyl-2,3-dihydro-1H-inden-5-olYield 46.1%

Reagents, catalysts & solvents 2

HCID 7108PhenothiazineCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

449 g of isoprene, stabilised with 1.3 g of phenothiazine, were added dropwise in the course of 7 hours to a solution of 732 g of 2,3-dimethyl-phenol, 76.5 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 of the mixture was continued overnight at 150° C. The acid phase was separated off and the organic phase was washed until neutral. Fractional distillation gave 526 g of 5-hydroxy-3,3,6,7-tetramethyl-indan; boiling point: 165°-167° C./15 mm Hg; melting point: 117°-118° C. ##STR7##

Workup

  1. customthe reaction
  2. customThe acid phase was separated off
  3. washthe organic phase was washed until neutral
  4. distillationFractional distillation

Sources & evidence

ORD record
ord-58318026963e4ccb9e1939faf8631afb
Source dataset
uspto-grants-1980_10
Patent number
US04228181

Reaction notes

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