o-Toluate → o-Propoxycarbonylbenzyltributylphosphonium bromide

HRID 1833295Notes

Reaction equation

HRID 1833295 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-36d545d8841c4e0e88fba35ecc7663ed
Source dataset
uspto-grants-1978_01
Patent number
US04066435

Reaction notes

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