Guaiacol → 6-Methoxy-3,3-dimethylindan-5-ol

HRID 2419769Notes

Reaction equation

HRID 2419769 reaction equation
[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].[C:6]1([O:13][CH3:14])[C:7](=[CH:9][CH:10]=[CH:11][CH:12]=1)[OH:8].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:11](=[CH:12][C:6]([O:13][CH3:14])=[C:7]([OH:8])[CH:9]=2)[CH2:1][CH2:2]1

Participants

7

Reactant 4

HCID 460GuaiacolHCID 962WaterHCID 1004Phosphoric AcidHCID 6557Isoprene

Product 1

HCID 1197896-Methoxy-3,3-dimethylindan-5-olYield 38.4%

Reagents, catalysts & solvents 2

HCID 7108PhenothiazineCatalystHCID 7237O-XyleneSolvent

Procedure

449 g of isoprene, stabilized with 1.4 g of phenothiazine, were added dropwise over the course of 6 hours to a solution of 744 g of guaiacol, 76 g of 85% strength phosphoric acid and 6 ml of water in 1.4 liters of xylene at 110° C. To complete the reaction, stirring of the mixture was continued overnight at 110° C. The acid phase was separated off and extracted by shaking with toluene. The combined organic phases were washed until neutral. Fractional distillation gave 443 g of 3,3-dimethyl-5-hydroxy-6-methoxy-indane, boiling point: 145- 46° C/12 mm Hg, melting point 43.5° - 44.5° C. ##STR35##

Workup

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

Sources & evidence

ORD record
ord-33317a64cd5c417abc04e583d6ee2f58
Source dataset
uspto-grants-1978_08
Patent number
US04107324

Reaction notes

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