Benzoic Acid → 1,1-Dimethylethyl benzoate

HRID 1578537Notes

Reaction equation

HRID 1578537 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[C:6](O)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1C=C2N=C(SSC3SC4C(=CC=CC=4)N=3)SC2=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 6386tert-ButanolHCID 8447Accelerator DMHCID 11776Triphenylphosphine

Product 1

HCID 698861,1-Dimethylethyl benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 0.74 g. of t-butanol, 1.22 g. of benzoic acid, 3.32 g. of 2,2'-dibenzothiazolyl disulfide and 50 ml. of methylene chloride is added dropwise a solution of 2.62 g. of triphenyl phosphine in 20 ml. of methylene chloride while stirring at room temperature. After completion of the addition, the mixture is stirred at room temperature for an additional 5 hours. The reaction mixture is treated with the same procedure as in Example 1 (1) to give 1.35 g. of the desired product boiling at 75°C/3 mmHg.

Workup

  1. additionTo a mixture of 0.74 g
  2. additionAfter completion of the addition
  3. customto give 1.35 g

Sources & evidence

ORD record
ord-1d64a254fe06435fbbbb6c66de065846
Source dataset
uspto-grants-1976_02
Patent number
US03937718

Reaction notes

Loading…