1,4-Butanediol → HCID 86748171, compound

HRID 1707321Notes

Reaction equation

HRID 1707321 reaction equation
[OH:1][C@H:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH2:9]([OH:14])[CH2:10][CH2:11][CH2:12][OH:13].C([Sn](=O)CCCC)CCC>>[OH:1][C@H:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH2:9]([OH:14])[CH2:10][CH2:11][CH2:12][OH:13]

Participants

4

Reactant 3

HCID 80641,4-ButanediolHCID 61221Dibutyltin oxideHCID 2724279Methyl 3-hydroxybutyrate, (R)-2×

Product 1

HCID 86748171HCID 86748171, compoundYield 90.4%

Conditions

Temperature
140 °C

Procedure

In a 200 ml reactor were charged 105.5 g (0.893 mol) of methyl (R)-3-hydroxybutyrate (hereinafter abbreviated as (R)-3HB), 8.05 g (0.0893 mol) of 1,4-butanediol, and 0.45 g (1.80 mmol) of dibutyltin oxide, and the mixture was distilled at 130° C. for 3 hours in a nitrogen stream to remove methanol. The pressure was gradually diminished to 0.5 mmHg, and the reaction mixture was stirred at 140° C. under that reduced pressure for 5 hours to obtain 76.8 g (percent yield: 90.4%) of the titled oligomer.

Workup

  1. distillationthe mixture was distilled at 130° C. for 3 hours in a nitrogen
  2. customto remove methanol

Sources & evidence

ORD record
ord-1c72fc291155445582aa67762add3571
Source dataset
uspto-grants-1994_10
Patent number
US05352763

Reaction notes

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