Hydrochloric Acid → 3-Hydroxybutyl 2,2-dimethylpropanoate

HRID 1199847Notes

Reaction equation

HRID 1199847 reaction equation
[CH2:1]([OH:6])[CH2:2][CH:3]([OH:5])[CH3:4].N1C=CC=CC=1.[C:13](Cl)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].Cl>ClCCl.O>[C:14]([C:13]([O:6][CH2:1][CH2:2][CH:3]([OH:5])[CH3:4])=[O:18])([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 78961,3-ButanediolHCID 62493Pivaloyl chloride

Product 1

HCID 150032733-Hydroxybutyl 2,2-dimethylpropanoateYield 78.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 13.2 ml (0.15 mol) of (±)-1,3-butandiol 24 and 17.8 ml (0.23 mol) of pyridine in 200 ml of dry dichloromethane is added a solution of 22.2 ml (0.18 mol) of pivaloyl chloride in 50 ml of dry dichloromethane dropwise over 20 minutes under ice cooling. Then, the mixture is stirred for additional 30 minutes at room temperature. Ice-cooled water is added and the mixture is stirred for 5 minutes and then 1N hydrochloric acid is added thereto. The mixture is extracted with dichloromethane twice. The extract is washed with water, a saturated aqueous solution of sodium hydrogencarbonate, and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue is purified by column chromatography on silica gel (250 g of silica gel, ethyl acetate:n-hexane=1:9 to 1:4) to give 20.4 g of the desired monopivaloyl ester 25 as an oil in 78.2% yield.

Workup

  1. additionis added
  2. stirringthe mixture is stirred for 5 minutes
  3. extractionThe mixture is extracted with dichloromethane twice
  4. washThe extract is washed with water
  5. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue is purified by column chromatography on silica gel (250 g of silica gel, ethyl acetate:n-hexane=1:9 to 1:4)

Sources & evidence

ORD record
ord-0467d58ee79742ec8d33e204493d0533
Source dataset
uspto-grants-1990_02
Patent number
US04902811

Reaction notes

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