Trimethyl orthoformate → 3-(2-Propenyl)-2-tetralone Ethylene Ketal

HRID 1421895Notes

Reaction equation

HRID 1421895 reaction equation
[CH2:1]([CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C:5]1=[O:14])[CH:2]=[CH2:3].C(OC)(OC)OC.[CH:22](O)([OH:24])[CH3:23]>ClCCl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:22]1[O:24][C:5]2([CH:4]([CH2:1][CH:2]=[CH2:3])[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6]2)[O:14][CH2:23]1

Participants

6

Reactant 3

HCID 9005Trimethyl orthoformateHCID 1512111,1-EthanediolHCID 102415333-(2-Propenyl)-2-tetralone

Product 1

HCID 571820293-(2-Propenyl)-2-tetralone Ethylene KetalYield 109%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(2-propenyl)-2-tetralone (25.9 g, 139 mmol), trimethyl orthoformate (61.3 ml, 554 mmol), ethanediol (57.5 ml, 1.03 mol), p-toluenesulfonic acid monohydrate (0.27 mg, 1.4 mmol) in dichloromethane (650 ml) was stirred at room temperature, under argon for 2 h. Resulting mixture was partitioned between saturated aqueous sodium bicarbonate (1000 ml) and dichloromethane (3×500 ml). The combined organic extracts were washed with brine (500 ml), dried (Na2SO4) and evaporated in vacuo to give a brown oil (34.9 g). Chromatography on silica using 0-10% ether-hexane gradient elution gave the title compound as a yellow oil (20.1 g, 63%).

Workup

  1. customResulting mixture
  2. customwas partitioned between saturated aqueous sodium bicarbonate (1000 ml) and dichloromethane (3×500 ml)
  3. washThe combined organic extracts were washed with brine (500 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-46faf412e4d44d34b9ddfceabd90e2e8
Source dataset
uspto-grants-2000_06
Patent number
US06080752

Reaction notes

Loading…