M-Cresol → 3,3,7-Trimethyl-2,3-dihydro-1H-inden-5-ol

HRID 2419771Notes

Reaction equation

HRID 2419771 reaction equation
[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].C1C2NC3C(=CC=CC=3)SC=2C=CC=1.[CH:20]1[C:25]([OH:26])=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:27].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](=[C:21]([CH3:27])[CH:20]=[C:25]([OH:26])[CH:24]=2)[CH2:1][CH2:2]1

Participants

7

Reactant 4

HCID 342M-CresolHCID 1004Phosphoric AcidHCID 6557IsopreneHCID 7108Phenothiazine

Product 1

HCID 30175523,3,7-Trimethyl-2,3-dihydro-1H-inden-5-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

449 of isoprene, stabilized with 1.35 g of phenothiazine, were added dropwise over the course of 7 hours to a solution of 648 g of m-cresol, 77 g of 85% strength phosphoric acid and 6 ml of water in 1.44 liters of xylene at 110° C. To complete the reaction, stirring was continued overnight at 110° 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 gave 252 g of 3,3,7-trimethyl-5-hydroxy-indane; boiling point 151°-155° C/18 mm Hg; melting point 80° - 81° C. ##STR37##

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-b6223ff6f53c472283cc639838d7ab5a
Source dataset
uspto-grants-1978_08
Patent number
US04107324

Reaction notes

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