O-Cresol → 3,3,6-Trimethyl-2,3-dihydro-1H-inden-5-ol

HRID 2419768Notes

Reaction equation

HRID 2419768 reaction equation
[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].C1C2NC3C(=CC=CC=3)SC=2C=CC=1.[C:20]1([CH3:27])[C:25]([OH:26])=[CH:24][CH:23]=[CH:22][CH:21]=1.P(=O)(O)(O)O>C1(C)C(C)=CC=CC=1.O>[CH3:4][C:3]1([CH3:5])[C:23]2[C:22](=[CH:21][C:20]([CH3:27])=[C:25]([OH:26])[CH:24]=2)[CH2:1][CH2:2]1.[CH3:4][C:3]1([CH3:5])[C:21]2[C:22](=[CH:23][CH:24]=[C:25]([OH:26])[C:20]=2[CH3:27])[CH2:1][CH2:2]1

Participants

8

Reactant 4

HCID 335O-CresolHCID 1004Phosphoric AcidHCID 6557IsopreneHCID 7108Phenothiazine

Product 2

HCID 30175493,3,6-Trimethyl-2,3-dihydro-1H-inden-5-olHCID 30175503,3,4-Trimethyl-2,3-dihydro-1H-inden-5-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

370 g of isoprene, stabilized with 1 g of phenothiazine, were added dropwise over the course of 6 hours to a solution of 535 g of o-cresol, 63 g of 85% strength phosphoric acid and 5 ml of water in 1.2 liters of xylene at 110° C. To complete the reaction, stirring was continued overnight at 110° C. The acid phase was separated off and extracted with toluene. The combined organic phases were washed until neutral. Fractional distillation gave 270 g of 3,3,6-trimethyl-5-hydroxy-indane (boiling point: 142°-143° C/12 mm Hg; melting point: 70° - 71° C) and 179 g of 3,3,4-trimethyl-5-hydroxy-indane (boiling point: 146° C/12 mm Hg; melting point 92° - 93° C). ##STR33##

Workup

  1. customthe reaction
  2. customThe acid phase was separated off
  3. extractionextracted with toluene
  4. washThe combined organic phases were washed until neutral
  5. distillationFractional distillation

Sources & evidence

ORD record
ord-a7eb7e54c0794a288a8c86986d572ef8
Source dataset
uspto-grants-1978_08
Patent number
US04107324

Reaction notes

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