Hydrochloric Acid → 2-Hydroxyethyl Methacrylate

HRID 1393530Notes

Reaction equation

HRID 1393530 reaction equation
[C:1]([O:6][CH2:7][CH2:8][OH:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.Cl.[OH-].[Na+]>>[O:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]1[O:5][CH:1]1[CH2:2][CH2:4][CH2:8][CH2:7][O:6]1.[C:1]([O:6][CH2:7][CH2:8][OH:9])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80803,4-dihydro-2H-pyranHCID 133602-Hydroxyethyl MethacrylateHCID 14798Sodium Hydroxide

Product 2

HCID 133602-Hydroxyethyl MethacrylateHCID 263182Tetrahydropyranyl ether

Procedure

A screw mouth-type bottle containing 55.4 g (0.43 mol) of hydroxyethyl methacrylate (trade name: Acryester HO; manufactured by Mitsubishi Rayon Co., Ltd.) and 37.0 g (0.44 mol) of dihydropyran (trade name: 3,4-Dihydro-2H-pyran; manufactured by Wako Pure Chemical Industries, Ltd.) is tightly closed by a rubber plug (Biton plug) and immersed in an ice bath. 0.47 g of concentrated hydrochloric acid is further added to the mixture, and the mixture is stirred at room temperature for 6 hours. The obtained reaction solution is passed through a column filled with sodium hydroxide to obtain a tetrahydropyranyl ether in which the OH group of hydroxyethyl methacrylate is protected by a protecting group.

Workup

  1. customis tightly closed by a rubber plug (Biton plug)
  2. customimmersed in an ice bath
  3. customThe obtained reaction solution

Sources & evidence

ORD record
ord-9778b2b9b949410c9bb70ca098cd61f4
Source dataset
uspto-grants-2008_03
Patent number
US07345126B2

Reaction notes

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