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Sulfuric Acid → 1-(Biphenyl-4-yl)cyclopropanecarboxylic acid isopropyl ester

HRID 2391050
Notes
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Reaction equation

HRID 2391050 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][C:4]([C:7]2([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.S(Cl)(Cl)=O.S(=O)(=O)(O)O.[CH:28](O)([CH3:30])[CH3:29]>>[CH:28]([O:11][C:10]([C:7]1([C:4]2[CH:5]=[CH:6][C:1]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:2][CH:3]=2)[CH2:9][CH2:8]1)=[O:12])([CH3:30])[CH3:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 24386Thionyl ChlorideHCID 215522631-(4-Biphenylyl)cyclopropanecarboxylic acid

Product 1

HCID 666602081-(Biphenyl-4-yl)cyclopropanecarboxylic acid isopropyl ester

Conditions

Temperature
65 °C

Procedure

1-(Biphenyl-4-yl)cyclopropanecarboxylic acid (10 g, 42 mmol), isopropanol (100 mL), thionyl chloride (6.8 mL, 92 mmol) were heated to 65° C. for 4 hours. Sulfuric acid (20 mL) was added and heated at 65° C. overnight. The product is extracted with CH2Cl2 and water (2×) dried and evaporated to yield 10.8 g of the title compound.

Workup

  1. extractionThe product is extracted with CH2Cl2 and water (2×)
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-e8c57432ab874836b273f20700b2efb1
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08273780B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes