Hydrochloric Acid → HCID 73880358, compound

HRID 966863Notes

Reaction equation

HRID 966863 reaction equation
CC(C)([O-])C.[K+].CCO[CH:10]([O:19]CC)[C:11]1[CH:16]=[CH:15][C:14]([CH:17]=O)=[CH:13][CH:12]=1.[Br-].[C:23]1([N:29]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:30]2[CH:49]=[CH:48][C:33]([CH2:34][P+](CCCC)(CCCC)CCCC)=[CH:32][CH:31]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>C1COCC1>[C:50]1([N:29]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:30]2[CH:49]=[CH:48][C:33]([CH:34]=[CH:17][C:14]3[CH:13]=[CH:12][C:11]([CH:10]=[O:19])=[CH:16][CH:15]=3)=[CH:32][CH:31]=2)[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5959934-(Diethoxymethyl)benzaldehydeHCID 22292433HCID 22292433, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 73880358HCID 73880358, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (0.044 mol, 44mL 1M solution in THF) was added to a mixture of terephthalaldehyde mono-(diethyl acetal) (Sigma-Aldrich) (9.98 g, 0.048 mol) and 4-(diphenylamino)benzyltributylphosphonium bromide (21.6 g, 0.040 mol) in anhydrous THF (200 mL) in a 500 mL round bottom flask equipped with a reflux condenser, addition funnel and nitrogen inlet. After the addition was complete, the mixture was refluxed for 2 hours, and then cooled to RT. Aqueous HCl (20 mL, 3M) was then added and the mixture was stirred an additional hour. The product was extracted with methylene chloride (3×100 mL) and the combined organic solution dried with MgSO4. The solvent was removed by rotovaporization and the crude product purified by silica gel column chromatography (1:1 hexane:methylene chloride) yielding the pure product as a bright yellow solid (13 g, 87%). 1H NMR δ: 7.02-7.85 (m, 18 Ar—H, 2 vinyl H), 9.96 (s, 1H, CHO).

Workup

  1. customequipped with a reflux condenser, addition funnel and nitrogen inlet
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed for 2 hours
  4. extractionThe product was extracted with methylene chloride (3×100 mL)
  5. dry with materialthe combined organic solution dried with MgSO4
  6. customThe solvent was removed by rotovaporization
  7. customthe crude product purified by silica gel column chromatography (1:1 hexane:methylene chloride)

Sources & evidence

ORD record
ord-c6e921f6f3474b4090c23d25579a6c56
Source dataset
uspto-grants-2005_10
Patent number
US06953570B2

Reaction notes

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