Triethylamine → HCID 15086716, compound

HRID 1111187Notes

Reaction equation

HRID 1111187 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([OH:13])=[C:7]([CH2:14][C:15]([CH3:17])=[CH2:16])[C:6]=1[CH3:18])(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:27])C=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:4][C:5]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]2[O:13][C:15]([CH2:17][OH:27])([CH3:16])[CH2:14][C:7]=2[C:6]=1[CH3:18])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 15086714HCID 15086714, compound

Product 1

HCID 15086716HCID 15086716, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (100 ml) was dissolved 4-acetoxy-2-(2-methyl-2-propenyl)-3,5,6-trimethylphenol [30 g (40.3 mmol)]. To the solution was added at 0° C., in limited amounts, m-chloroperbenzoic acid [16.7 g (67.8 mmol)]. The reaction mixture was stirred for one hour, and there was added triethylamine (30 ml), followed by stirring for further one hour. The reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate, and then dried, followed by distilling off the solvent. The residue was crystallized from isopropyl ether-hexane to obtain the desired 5-acetoxy-2-hydroxymethyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran [9.3 g (yield 87.4%, m.p. 98°-99° C.)].

Workup

  1. stirringby stirring for further one hour
  2. washThe reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate
  3. customdried
  4. distillationby distilling off the solvent
  5. customThe residue was crystallized from isopropyl ether-hexane

Sources & evidence

ORD record
ord-1bf48b76f4104bc488bb40bb8df913c7
Source dataset
uspto-grants-1990_12
Patent number
US04978761

Reaction notes

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