Water → HCID 12363892, compound

HRID 1419907Notes

Reaction equation

HRID 1419907 reaction equation
C1(C(C2[C:14]([CH2:15][O:16][CH2:17][C:18]3[C:23](C4C(=CC=C(O)C=4)O)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=[CH:11][CH:10]=2)=CC(=CC=1)O)O.[CH2:32]([C@H:34]1[O:36][CH2:35]1)Cl.[OH2:37]>[Cl-].C[N+](C)(C)C.C(Cl)Cl>[C:18]1([CH2:17][O:16][C:15]2[CH:10]=[CH:11][C:12]([O:37][CH2:32][C@H:34]3[CH2:35][O:36]3)=[CH:13][CH:14]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 962WaterHCID 149428(+)-EpichlorohydrinHCID 1317110222-[2-[[2-(2,5-Dihydroxyphenyl)phenyl]methoxymethyl]phenyl]benzene-1,4-diol

Product 1

HCID 12363892HCID 12363892, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6379Tetramethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of hydroquinone monobenzylether (1.7 g, 8.5 mmol) and tetramethylammoniumchloride (0.19 g, 1.7 mmol) in (S)-epichlorohydrine (2.0 ml, 25.5 mmol) was stirred at room temperature for 4 days. H2O (30 ml) and CH2Cl2 (50 ml) were added and the organic phase was separated. The water phase was extracted two times with CH2Cl2. The organic phases were then pooled, dried with Na2SO4 and the solvent evaporated. The residue was chromatographed over silica gel (hexane-Et2O, 3:1) to give (R)-{[4-(Phenylmethoxy)phenoxy]methyl}-oxirane (1.1 g, 50%) as a colorless solid, m.p. 70°-73° C., [α]D20 =-8.1° (c=1.0, methanol) and MS: m/e=256 (M+).

Workup

  1. customthe organic phase was separated
  2. extractionThe water phase was extracted two times with CH2Cl2
  3. dry with materialdried with Na2SO4
  4. customthe solvent evaporated
  5. customThe residue was chromatographed over silica gel (hexane-Et2O, 3:1)

Sources & evidence

ORD record
ord-2ae13c4ea2274754b1831af9c57380ef
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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