Sulfuric Acid → tert-Butyl cyclohexa-2,5-diene-1-carboxylate

HRID 1448817Notes

Reaction equation

HRID 1448817 reaction equation
[CH:1]1([C:7]([OH:9])=[O:8])[CH:6]=[CH:5][CH2:4][CH:3]=[CH:2]1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>ClCCl.CC(=C)C>[CH:1]1([C:7]([O:9][C:1]([CH3:7])([CH3:6])[CH3:2])=[O:8])[CH:6]=[CH:5][CH2:4][CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 78522Cyclohexa-2,5-diene-1-carboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 12375195tert-Butyl cyclohexa-2,5-diene-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneCatalystHCID 8255IsobutyleneSolvent

Procedure

A solution of 16 g of 2,5-cyclohexadiene carboxylic acid in 20 ml of dichloromethane containing 10 drops of sulfuric acid is treated with 40 ml of isobutylene in an autoclave overnight after which the contents were poured into a sodium bicarbonate solution. The organic phase is isolated and passed through alumina to afford tert-butyl 2,5-cyclohexadienecarboxylate.

Workup

  1. customThe organic phase is isolated

Sources & evidence

ORD record
ord-c7c5e82b84a04e319e31c26b8799c59c
Source dataset
uspto-grants-1980_02
Patent number
US04187316

Reaction notes

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