o-Toluate → o-Propoxycarbonylbenzyltributylphosphonium bromide

HRID 972557Notes

Reaction equation

HRID 972557 reaction equation
Cl[CH2:2][C:3]1[C:4]([C:9]([O:11][CH2:12][CH2:13][CH3:14])=[O:10])=[CH:5][CH:6]=[CH:7][CH:8]=1.[Br:15]CC1C(C(OCCC)=O)=CC=CC=1.BrCC1C(C(Cl)=O)=CC=CC=1.C1(C)C(C([O-])=O)=CC=CC=1.[Br-].CO[C:53]([C:55]1C=CC=C[C:56]=1[CH2:57][P+:58](CCCC)([CH2:63][CH2:64][CH2:65][CH3:66])[CH2:59][CH2:60][CH2:61][CH3:62])=O>C(O)CC>[Br-:15].[CH2:12]([O:11][C:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][P+:58]([CH2:59][CH2:60][CH2:61][CH3:62])([CH2:63][CH2:64][CH2:65][CH3:66])[CH2:57][CH2:56][CH2:55][CH3:53])=[O:10])[CH2:13][CH3:14]

Participants

7

Reactant 5

HCID 6997338o-ToluateHCID 122516322-Bromomethylbenzoyl chlorideHCID 18464439Propyl alpha-chloro-o-toluateHCID 21388617Propyl alpha-bromo-o-toluateHCID 21388625o-Methoxycarbonylbenzyltributylphosphonium bromide

Product 1

HCID 21388593o-Propoxycarbonylbenzyltributylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

Using the procedure of Example V, but substituting a mixture of propyl α-chloro-o-toluate and propyl α-bromo-o-toluate, prepared from propyl alcohol and α-bromo-o-toluoyl chloride, for the toluate mixture of Example V provides an oil which upon triturating several times with ether and precipitating as an oil from ethyl acetate with ether and drying yields 18.7 g of o-propoxycarbonylbenzyltributylphosphonium bromide, an oil having a structure in accordance with formula (1) which is confirmed by nmr spectral analysis.

Workup

  1. customprovides an oil which
  2. customupon triturating several times with ether
  3. customprecipitating as an oil from ethyl acetate with ether
  4. customdrying

Sources & evidence

ORD record
ord-c7b00b8a7e3045f99132c12e699a7049
Source dataset
uspto-grants-1977_10
Patent number
US04053501

Reaction notes

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