Water → 3,3-Dimethylindan-5-ol

HRID 2419765Notes

Reaction equation

HRID 2419765 reaction equation
[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].[C:6]1([OH:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.P(=O)(O)(O)O.O>C1(C)C(C)=CC=CC=1.C1C2NC3C(=CC=CC=3)SC=2C=CC=1>[CH3:4][C:3]1([CH3:5])[C:10]2[C:9](=[CH:8][CH:7]=[C:6]([OH:12])[CH:11]=2)[CH2:1][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 1004Phosphoric AcidHCID 6557Isoprene

Product 1

HCID 786603,3-Dimethylindan-5-olYield 33.1%

Reagents, catalysts & solvents 2

HCID 7108PhenothiazineCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
110 °C

Procedure

322 g of isoprene, stabilized with 1 g of phenothiazine, were added dropwise over the course of 8 hours to a solution of 403 g of phenol, 50 g of 85% strength phosphoric acid and 9 ml of water in 2.14 liters of xylene at 110° C. To complete the reaction, the mixture was stirred overnight at 110° C. The acid phase was separated off and the organic phase was washed until neutral. Fractional distillation gave 230 g of 3,3-dimethyl-5-hydroxy-indane, boiling point 132°-134° C/10 mm Hg; melting point 84.5° -86.5° C. ##STR30##

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-1951b4c026074b19820d15e0600722e6
Source dataset
uspto-grants-1978_08
Patent number
US04107324

Reaction notes

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