Benzyl Alcohol → Benzyl hexanoate

HRID 1578536Notes

Reaction equation

HRID 1578536 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](O)(=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C1C=C(SSC2N=CC=CC=2)N=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8892Hexanoic AcidHCID 11776TriphenylphosphineHCID 650932,2'-Dipyridyl disulfide

Product 1

HCID 23367Benzyl hexanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 1.08 g. of benzylalcohol, 1.16 g. of caproic acid, 2.20 g. of 2,2'-dipyridyl 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 3 hours. The reaction mixture is treated with the same procedure as in Example 1 (1) to give 1.9 g. of the desired product boiling at 75°C/0.2 mmHg.

Workup

  1. additionTo a mixture of 1.08 g
  2. additionAfter completion of the addition
  3. customto give 1.9 g

Sources & evidence

ORD record
ord-5ef232b4bebd43bab0efd7dd2af2e21f
Source dataset
uspto-grants-1976_02
Patent number
US03937718

Reaction notes

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