Triphenylphosphonium bromide → HCID 23349110, compound

HRID 1855795Notes

Reaction equation

HRID 1855795 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[C:5]([CH3:9])[C:6]=1[CH2:7]O.[BrH:10].[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCl>[Br-:10].[CH3:1][C:2]1[O:3][CH:4]=[C:5]([CH3:9])[C:6]=1[CH2:7][P+:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 80811Triphenylphosphonium bromideHCID 12858598(2,4-Dimethylfuran-3-yl)methanol

Product 1

HCID 23349110HCID 23349110, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,4-dimethyl-3-hydroxymethylfuran (11 g.) in dichlormethane (25 ml.) was added to a cooled slurry of triphenylphosphine hydrobromide (34 g.) in dichloromethane to give a clear solution. After standing a further 30 minutes at room temperature the bulk of the solvent was distilled off and the residue was crystallized from a 1:4 parts by volume mixture of methanol and ethylacetate to yield a buff colored solid (27.2 g.) of (2,4-dimethyl-3-furyl)methyl triphenylphosphonium bromide, m.p. 248°-249°.

Workup

  1. customto give a clear solution
  2. distillationthe bulk of the solvent was distilled off
  3. customthe residue was crystallized from a 1:4 parts by volume mixture of methanol and ethylacetate

Sources & evidence

ORD record
ord-1ac26b488ab24fdea2f0fe98f069f792
Source dataset
uspto-grants-1980_08
Patent number
US04216312

Reaction notes

Loading…