Ethylene Glycol → 4-[(5,6-Dihydro-5,5-dimethyl-8-(2-furyl)-2-naphthalenyl)ethynyl]benzoic acid

HRID 618079Notes

Reaction equation

HRID 618079 reaction equation
[CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[CH:7][C:8]([C:12](=O)[CH3:13])=[CH:9][CH:10]=2)[C:5](=O)[CH2:4][CH2:3]1.CC1(C)[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:28](=[O:30])C)[CH:26]=2)C(=O)CC1.[CH2:33]([OH:36])[CH2:34]O.[OH2:37].[C:38]1(C)C=CC(S(O)(=O)=O)=C[CH:39]=1>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:16])[CH2:3][CH:4]=[C:5]([C:38]2[O:36][CH:33]=[CH:34][CH:39]=2)[C:6]2[CH:7]=[C:8]([C:12]#[C:13][C:22]3[CH:23]=[CH:24][C:25]([C:28]([OH:30])=[O:37])=[CH:26][CH:27]=3)[CH:9]=[CH:10][C:11]1=2

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 111067823,4-dihydro-4,4-dimethyl-6-acetyl-1(2H)-naphthalenone2×HCID 223237263,4-dihydro-4,4-dimethyl-7-acetyl-1(2H)-naphthalenone2×

Product 1

HCID 158709544-[(5,6-Dihydro-5,5-dimethyl-8-(2-furyl)-2-naphthalenyl)ethynyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1.80 g (8.34 mmol) of a 1:5 mixture of 3,4-dihydro-4,4-dimethyl-7-acetyl-1(2H)-naphthalenone (Compound 100C); and 3,4-dihydro-4,4-dimethyl-6-acetyl-1(2H)-naphthalenone (Compound 100D) in 50 ml benzene was combined with 517.7 mg (8.34 mmol) of ethylene glycol and 20.0 mg (0.11 mmol) of p-toluenesulfonic acid monohydrate. The resulting solution was heated to reflux for 18 hours, cooled to room temperature, and concentrated under reduced pressure. The title compound was isolated by column chromatography (10% EtOAc-hexanes) as a colorless oil. 1H NMR (CDCl3): δ 8.01 (1H, d, J=8.2 Hz), 7.51 (1H, s), 7.43 (1H, dd, J=1.7, 6.4 Hz), 4.07 (2H, m), 3.79 (2H, m), 2.74 (2H, t, J=6.5 Hz), 2.04 (2H, t, J=7.1 Hz), 1.67 (3H, s), 1.46 (6H, s).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 18 hours
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f7f81967912b45658ca4febe918a4df2
Source dataset
uspto-grants-1999_09
Patent number
US05952345

Reaction notes

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