Hydrochloric Acid → HCID 54005412, compound

HRID 361299Notes

Reaction equation

HRID 361299 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[CH2:15]([Mg]Br)[CH:16]=[CH2:17].Cl>C1COCC1.CCOCC>[OH:6][CH:5]([C:4]1[CH:7]=[CH:8][C:9]([O:13][CH3:14])=[C:10]([O:11][CH3:12])[C:3]=1[O:2][CH3:1])[CH2:17][CH:16]=[CH2:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 750062,3,4-TrimethoxybenzaldehydeHCID 178455850HCID 178455850, compound

Product 1

HCID 54005412HCID 54005412, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 8.77 g (44.7 mmol) of 2,3,4-trimethoxybenzaldehyde in 100 mL of THF was cooled in an ice bath and 55 mL of 1.0 molar (55.0 mmol) allylmagnesium bromide in ether was added dropwise over 0.5 h. The cooling bath was allowed to warm up and the mixture was stirred overnight at room temperature. A 200 mL portion of 5% aqueous HCl was added and the mixture was extracted with two 200 mL portions of ether. The combined ether extracts were washed with 50 mL of saturated aqueous NaHCO3, dried over MgSO4 and the solvent removed in vacuo to leave 10.30 g of 4-hydroxy-4-(2,3,4-trimethoxyphenyl)butene as an oil. 1H NMR (CDCl3) d 2.5 (m, 2H), 3.8 (s, 6H), 3.9 (s, 3H), 4.9 (t, 1H), 5.1 (m, 2H), 5.85 (m, 1H), 6.65 (d, 1H), 7.05 (d, 1H).

Workup

  1. temperatureto warm up
  2. extractionthe mixture was extracted with two 200 mL portions of ether
  3. washThe combined ether extracts were washed with 50 mL of saturated aqueous NaHCO3
  4. dry with materialdried over MgSO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-33eaa137d0f34b95a7c92a54accb5f2b
Source dataset
uspto-grants-1999_02
Patent number
US05866513

Reaction notes

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