p-Toluenesulfonic acid → Benzoic acid, 4-(hydroxymethyl)-3-nitro-, 2-propenyl ester

HRID 850268Notes

Reaction equation

HRID 850268 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].[C:15]1(C)[CH:20]=CC(S(O)(=O)=O)=C[CH:16]=1>C(O)C=C>[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH2:20][CH:15]=[CH2:16])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15018924-Hydroxymethyl-3-nitrobenzoic acid

Product 1

HCID 11118069Benzoic acid, 4-(hydroxymethyl)-3-nitro-, 2-propenyl ester

Reagents, catalysts & solvents 1

HCID 7858Allyl AlcoholSolvent

Procedure

In a 100 mL round bottom flask was placed 4-hydroxymethyl-3-nitrobenzoic acid (1.97 g, 10 mmol). Allyl alcohol (20 mL) was added, followed by p-toluenesulfonic acid (0.190 g, l mmol). The mixture was heated to reflux for 24 hr., at which time all the volatiles were removed in vacuo. The residue was taken up in EtOAc and washed with sat'd KHCO3. The organic layer was dried over MgSO4 and concentrated to afford the title compound as a cream colored solid; 2.4 g (100%).

Workup

  1. customIn a 100 mL round bottom flask was placed
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 24 hr
  4. custom, at which time all the volatiles were removed in vacuo
  5. washwashed with sat'd KHCO3
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6e36e1f038a64b0c831ec2635cb9b3c4
Source dataset
uspto-grants-2000_01
Patent number
US06017768

Reaction notes

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