Sulfuric Acid → HCID 21840284, compound

HRID 1739046Notes

Reaction equation

HRID 1739046 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:11]([O:14][C:15]1[CH:27]=[CH:26][C:18]([CH:19]=[CH:20][C:21](OCC)=[O:22])=[CH:17][C:16]=1[O:28][CH3:29])([CH3:13])[CH3:12].S(=O)(=O)(O)O>C(OCC)C.C(OCC)C.O1CCCC1.O>[CH:11]([O:14][C:15]1[CH:27]=[CH:26][C:18](/[CH:19]=[CH:20]/[CH2:21][OH:22])=[CH:17][C:16]=1[O:28][CH3:29])([CH3:13])[CH3:12]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 53753228HCID 53753228, compound

Product 1

HCID 21840284HCID 21840284, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 21868444Ether tetrahydrofuranSolvent

Procedure

A solution of aluminium chloride (AlCl3) (6.1 g) in diethyl ether (70 ml) was added dropwise to a suspension of lithium aluminum hydride (LiAlH4) (6.4 g) in diethyl ether (270 ml) at 0° C., and the mixture was stirred at room temperature for 10 minutes. Then, a solution of ethyl 4-isopropoxy-3-methoxycinnamate (35.4 g) in diethyl ether-tetrahydrofuran (3:1, 220 ml) was added dropwise at room temperature. The mixture was stirred at room temperature for 2 hours. Then water (170 ml) and 6N sulfuric acid (270 ml) were added dropwise under ice-cooling, and the organic layer was separated, and the aqueous layer was extracted with diethyl ether. The organic layers were combined, washed with water, dried over magnesium sulfate, and concentrated. The residue was subjected to chromatography on silica gel. The fractions eluted with ethyl acetate-hexane (1:2, v/v) gave (E)-3-(4-isopropoxy-3-methoxyphenyl)-2-propenol (27.0 g, 91%) as an oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. temperaturecooling
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with diethyl ether
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. washThe fractions eluted with ethyl acetate-hexane (1:2

Sources & evidence

ORD record
ord-608b5b8e70174697a129a1df37d2e3c2
Source dataset
uspto-grants-1999_10
Patent number
US05965589

Reaction notes

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