Phosgene → HCID 20277501, compound

HRID 1248662Notes

Reaction equation

HRID 1248662 reaction equation
[C:1](Cl)(Cl)=[O:2].[C:5]1([CH2:11][CH:12]([OH:22])[CH:13]([OH:21])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C>C(OCC)C>[CH2:14]([CH:13]1[CH:12]([CH2:11][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[O:22][C:1](=[O:2])[O:21]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6371Phosgene2×HCID 8471TriethylamineHCID 30150041,4-Diphenylbutane-2,3-diol

Product 1

HCID 20277501HCID 20277501, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Phosgene gas was slowly bubbled into a solution of 1,4-diphenyl-2,3-butanediol (Neher (1963) Hel. Chim. Acta. 46:1083) (96 mg, 0.4 mmole) and triethylamine (0.16 ml, 1 mmole) in anhydrous ethyl ether (75 ml). After 15 min, the phosgene addition was stopped, the solution filtered, and the solvent removed in vacuo (20° C./60 mm Hg) leaving a crystalline residue, which was flash chromatographed (CH2Cl2 eluent) affording 4,5-dibenzyl-1,3-dioxolan-2-one as a colorless, crystalline compound (98 mg, 94%): mp 155°-156° C.; IR (KBr) 3020, 1783, 1200, 1166, 1150, 1092, 1067, 1030, 765, 755, 703 cm-1 ; 'H NMR (CDCl3) 2.88(m, 4H), 4.55(t, J=3 Hz, 2H), 7.33(m, 10H); MS (70 eV) C17H16O3 calcd. 268.3235 obsd. 268.1096.

Workup

  1. filtrationthe solution filtered
  2. customthe solvent removed in vacuo (20° C./60 mm Hg)
  3. customleaving a crystalline residue, which
  4. customchromatographed (CH2Cl2 eluent)

Sources & evidence

ORD record
ord-f41d9dbd76eb48af98a0eedfeb2adfce
Source dataset
uspto-grants-1985_06
Patent number
US04525540

Reaction notes

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