Water → HCID 17819694, compound

HRID 1937032Notes

Reaction equation

HRID 1937032 reaction equation
[C:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]1O)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[C:1]([C:5]1[CH2:13][C:12]2[C:7]([CH:6]=1)=[CH:8][CH:9]=[CH:10][CH:11]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 12927382HCID 12927382, compound

Product 1

HCID 17819694HCID 17819694, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2-t-butyl-1-indanol (8.19 g, 43.1 mmol) and p-toluenesulfonic acid (0.200 g, 1.05 mmol) in benzene was heated under reflux for 0.5 h. Water (20 mL) was added. Aqueous layer was extracted with ether (4*50 mL). All organic layers were combined, washed with water (20 mL), brine (10 mL) and concentrated to produce 7.41 g (100 g) of 2-t-butyl-indene. 1H-NMR (CDCl3) δ 1.18 (s, 9 H), 3.30 (s, 2H), 6.45 (s, 1H), 7.02 (tdd, J=7.3, 1.4, 0.3 Hz, 1H), 7.14 (br t, J=7.5 Hz, 1H), 7.19 (br d, J=7.3 Hz, 1H), 7.31 (br d, J=7.3 Hz, 1 H). 13C-NMR (CDCl3) δ 30.44, 33.45, 37.84, 120.09, 123.42, 123.50, 123.63, 126.25, 143.11, 145.49, 150.16.

Workup

  1. temperatureunder reflux for 0.5 h
  2. extractionAqueous layer was extracted with ether (4*50 mL)
  3. washwashed with water (20 mL), brine (10 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-217aa230f839422cbe68554a5d4ad3f5
Source dataset
uspto-grants-2002_05
Patent number
US06391991B1

Reaction notes

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