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p-Toluenesulfonic acid → (1R,cis) 2,2-dimethyl-3-[Z-2-(propargyloxycarbonyl)-ethenyl]-cyclopropane-carboxylic acid

HRID 1995180
Notes
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Reaction equation

HRID 1995180 reaction equation
[CH3:1][C:2]1([CH3:20])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH2:10][C:11]#[CH:12])=[O:8])[C@H:3]1[C:13]([O:15]C(C)(C)C)=[O:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:20])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH2:10][C:11]#[CH:12])=[O:8])[C@H:3]1[C:13]([OH:15])=[O:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86739014tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-(propargyloxy-carbonyl)-ethenyl]cyclopropane-carboxylate

Product 1

HCID 86739015(1R,cis) 2,2-dimethyl-3-[Z-2-(propargyloxycarbonyl)-ethenyl]-cyclopropane-carboxylic acidYield 99.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2.0 g of the product of Step A, 0.2 g of p-toluene sulfonic acid and 20 ml of anhydrous toluene was refluxed for 10 minutes and was cooled to 0° C. and stirred for 30 minutes. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure to obtain 1.59 g of (1R,cis) 2,2-dimethyl-3-[Z-2-(propargyloxycarbonyl)-ethenyl]-cyclopropane-carboxylic acid which was used as is for the next step.

Workup

  1. temperaturewas refluxed for 10 minutes
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-cb102b78465e4a5d955f898e5237f867
Source dataset
uspto-grants-1983_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04402972

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes