Formic Acid → HCID 21405851, compound

HRID 918265Notes

Reaction equation

HRID 918265 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=[O:9].N1C=CC=CC=1.[SH:17][C:18]([CH3:24])([CH3:23])[CH2:19][CH:20](O)[CH3:21]>C(OCC)C>[CH:8]([O:10][CH:20]([CH2:19][C:18]([SH:17])([CH3:24])[CH3:23])[CH3:21])=[O:9]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 64293084-Methyl-4-sulfanylpentan-2-ol

Product 1

HCID 21405851HCID 21405851, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 12.3 g of acetic anhydride and 6.2 g of formic acid was heated at 40°C for 1 hour. After cooling to 20°C 1 g of pyridine was added and subsequently, with stirring, 15 g of 4-mercapto-4-methylpentan-2-ol in the course of 10 minutes. The temperature of the reaction mixture slowly rose to 28°C. After standing overnight it was dissolved in diethylether, washed five times with 3% aqueous NaHCO3 solution and then with aqueous NaCl solution to neutral. The ethereal solution was dried over Na2SO4 and concentrated. Distillation of the residue yielded 10.5 g (58%) of 4-mercapto-4-methylpent-2-yl formate, b.p. 30°-32°C/1 mm, nD20 1.4564.

Workup

  1. additionwas added
  2. customin the course of 10 minutes
  3. customslowly rose to 28°C
  4. washwashed five times with 3% aqueous NaHCO3 solution
  5. dry with materialThe ethereal solution was dried over Na2SO4
  6. concentrationconcentrated
  7. distillationDistillation of the residue

Sources & evidence

ORD record
ord-4bb116fa0b2245a3bf09064b48e4eacc
Source dataset
uspto-grants-1976_07
Patent number
US03970689

Reaction notes

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