Potassium Hydroxide → 4-(2-Thienyl)-1-indanol

HRID 325777Notes

Reaction equation

HRID 325777 reaction equation
C([O:4][CH:5]1[C:13]2[C:8](=[C:9]([C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)(=O)C.[OH-].[K+]>O.C(O)C>[S:15]1[CH:16]=[CH:17][CH:18]=[C:14]1[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[CH2:7][CH2:6][CH:5]2[OH:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 131024594-(2-Thienyl)-1-indanyl acetate

Product 1

HCID 131024604-(2-Thienyl)-1-indanolYield 79.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To 3.5 g (0.014 mole) of 4-(2-thienyl)-1-indanyl acetate was added a solution of 1.1 g (0.019 mole) of potassium hydroxide in 19.5 mL of water and 39 mL of ethanol. The reaction mixture was stirred for three hours at 60°-70° C., then for 16 hours at ambient temperature. The reaction mixture was concentrated under reduced pressure to give an oil residue. The oil was slurried in 75 mL of water for one hour, causing the oil to solidify. The solid was washed with water, air dried, then recrystallized from toluene to give, in three crops, 2.4 g of 4-(2-thienyl)-1-indanol, m.p. 101°-103.5° C.

Workup

  1. waitfor 16 hours at ambient temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give an oil residue
  4. washThe solid was washed with water, air
  5. customdried
  6. customrecrystallized from toluene

Sources & evidence

ORD record
ord-4ae13ca609d242b1923838836a90919a
Source dataset
uspto-grants-1984_04
Patent number
US04442296

Reaction notes

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