Ethanol → Ethyl benzoate

HRID 1735599Notes

Reaction equation

HRID 1735599 reaction equation
[C:1]1(OP([O-])(OC2C=CC=CC=2)=O)C=CC=C[CH:2]=1.C([N+](CCCC)(CCCC)CCCC)CCC.[C:35]([O-:43])(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C([NH+](CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.S(Cl)(Cl)(=O)=O.C(O)C>N1C=CC=CC=1>[C:35]([O:43][CH2:1][CH3:2])(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 18319437HCID 18319437, compoundHCID 21903624HCID 21903624, compoundHCID 88435291HCID 88435291, compound

Product 1

HCID 7165Ethyl benzoateYield 16%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The applicant also examined whether other acids can be converted to acid chlorides by this reagent. Reaction of PPh3 /SO2Cl2 with tetra-n-butyl ammonium diphenyl phosphate followed by quenching with ethanol in pyridine led to the phosphate triester in 63% isolated yield, indicating that this reaction may also be useful for the activation of phosphate diesters under very mild conditions. The same reaction does not appear to be preferred for the synthesis of acid chlorides from carboxylates. For example, treatment of triethylammonium benzoate with PPh3 /sulfuryl chloride, followed by the addition of ethanol in pyridine gave ethyl benzoate in only 16% yield. These results indicate that less nucleophilic salts such as sulfate monoesters, or sulfamates are likely to be better substrates for this type of activation than more nucleophilic ones.

Workup

  1. customby quenching with ethanol in pyridine
  2. customisolated
  3. customyield
  4. customThe same reaction

Sources & evidence

ORD record
ord-0eb08d7ac6c04661a7cc84480679d9d1
Source dataset
uspto-grants-1996_07
Patent number
US05536823

Reaction notes

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