Ethylene Glycol → HCID 23498864, compound

HRID 1836901Notes

Reaction equation

HRID 1836901 reaction equation
[C:1]([O:4][CH:5]1[C:14]([CH3:16])([CH3:15])[C:13]2[CH:12]=[C:11]([CH:17]=[O:18])[C:10]([Br:19])=[CH:9][C:8]=2[C:7]([CH3:21])([CH3:20])[CH2:6]1)(=[O:3])[CH3:2].[CH2:22](O)[CH2:23][OH:24].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1.ClCCl>[C:1]([O:4][CH:5]1[C:14]([CH3:15])([CH3:16])[C:13]2[CH:12]=[C:11]([CH:17]3[O:24][CH2:23][CH2:22][O:18]3)[C:10]([Br:19])=[CH:9][C:8]=2[C:7]([CH3:21])([CH3:20])[CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 23498870HCID 23498870, compound

Product 1

HCID 23498864HCID 23498864, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

7-Acetoxy-3-bromo-2-formyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (0.3 g, 0.849 mmol) from the preceding reaction was dissolved in 2 mL of benzene. Ethylene glycol (0.104 mL, 1.87 mmol) and p-toluenesulfonic acid monohydrate (0.024 g, 0.127 mmol) were added. A Dean-Stark apparatus was attached to the reaction flask and the reaction was brought to reflux for several hours. When the reaction was judged complete by TLC (SiO2, 20% ethyl acetate/hexanes), dichloromethane (25 mL) and sodium bicarbonate solution (50 mL) were added and the layers were separated. The aqueous layer was extracted one more time with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to give 7-Acetoxy-3-bromo-2-(1,3-dioxolane-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene as an oily residue that was used directly in the next step.

Workup

  1. temperatureto reflux for several hours
  2. additionwere added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted one more time with dichloromethane
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5bcd21c1d60446ca9b90a438dd9b3fd3
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

Loading…