Toluene → HCID 86739816, compound

HRID 1383203Notes

Reaction equation

HRID 1383203 reaction equation
[CH3:1][C:2]1([CH3:19])[C@@H:4](/[CH:5]=[C:6](\[Br:11])/[C:7](=[O:10])[O:8][CH3:9])[C@H:3]1[C:12]([O:14]C(C)(C)C)=[O:13].C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[CH3:1][C:2]1([CH3:19])[C@@H:4](/[CH:5]=[C:6](\[Br:11])/[C:7](=[O:10])[O:8][CH3:9])[C@H:3]1[C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 86739817HCID 86739817, compound

Product 1

HCID 86739816HCID 86739816, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 3.3 g of the product of Step B, 30 ml of toluene and 0.33 g of p-toluene sulfonic acid monohydrate was refluxed until gas evolution ceased and was cooled to 20° C. and diluted with ether. The ether phase was washed with water, dried and evaporated to dryness at 40° C. under reduced pressure to obtain 2.9 g of (1R,cis) 2,2-dimethyl-3(Z)-[2-bromo-3-oxo-3-methoxy-propenyl]-cyclopropane-1-carboxylic acid.

Workup

  1. temperaturewas refluxed until gas evolution
  2. washThe ether phase was washed with water
  3. customdried
  4. customevaporated to dryness at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-7ce75a2f754348fda3456d48104319e2
Source dataset
uspto-grants-1989_02
Patent number
US04808749

Reaction notes

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