1-Butanol → HCID 15133031, compound

HRID 1086084Notes

Reaction equation

HRID 1086084 reaction equation
S(Cl)(Cl)=O.[CH:5]1([CH2:8][C:9]([OH:11])=[O:10])[CH2:7][CH2:6]1.[CH2:12](O)[CH2:13][CH2:14][CH3:15].C(N(CC)CC)C>CCOCC>[CH:5]1([CH2:8][C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 138440Cyclopropaneacetic acid

Product 1

HCID 15133031HCID 15133031, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Thionyl chloride (10.7 g, 90 mmol) was added to cyclopropaneacetic acid (9.0 g 90 mmol) [J. Med. Chem. 27, 1291 (1984); Chem. Lett., 1273 (1983); J. Org. Chem. 43. 3496 (1978)]. After stirring for 64 hours the liquid was dissolved in ether and added to a solution of butanol (6.7 g, 90 mmol) and triethylamine (9.1 g, 90 mmol) in 100 mL of diethyl ether at 0° C. The mixture was stirred for 16 hours and washed with water. The organic phase was dried over magnesium sulfate and concentrated in vacuo. The residue was distilled at 46° C. at 2 mm of Hg to give 7 g of the title compound. MS(CI): m/e =156 for M+ of C9H16O2.

Workup

  1. stirringThe mixture was stirred for 16 hours
  2. washwashed with water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. distillationThe residue was distilled at 46° C. at 2 mm of Hg

Sources & evidence

ORD record
ord-9fbdad11689f4e069684a54f4d4fb607
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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