Hydroquinone → (2-Methoxy-2-methyl-1,3-dioxolan-4-yl)methyl prop-2-enoate

HRID 1593726Notes

Reaction equation

HRID 1593726 reaction equation
[CH2:1]1[O:3][CH:2]1[CH2:4][OH:5].[C:6]([OH:10])(=[O:9])[CH:7]=[CH2:8].Cl.C(N([CH2:17][CH3:18])CC)C.[C:19]1(C=CC(O)=CC=1)[OH:20].C(O)(=O)C=C.C1(C=CC(O)=CC=1)O>>[C:6]([O:10][CH2:1][CH:2]1[CH2:4][O:5][C:17]([O:20][CH3:19])([CH3:18])[O:3]1)(=[O:9])[CH:7]=[CH2:8]

Participants

6

Reactant 5

HCID 785HydroquinoneHCID 6581Acrylic AcidHCID 11130Triethylamine hydrochlorideHCID 11164Glycidol2×HCID 68966952HCID 68966952, compound

Product 1

HCID 17748066(2-Methoxy-2-methyl-1,3-dioxolan-4-yl)methyl prop-2-enoateYield 63%

Conditions

Temperature
125 °C

Procedure

Glycidol and acrylic acid which comprises 6.4% by weight of triethylamine hydrochloride and 0.6% by weight of hydroquinone were metered together into a loop reactor heated to 125° C. The metering rate for glycidol was 40 g/h; that for the acrylic acid/hydroquinone/catalyst solution was 41 g/h. The residence time was approx. 15 min. The effluent of the loop reactor within one hour was collected, cooled and admixed with 69 g of trimethyl orthoacetate. The mixture was stirred at 25° C. for 1 hour. A crude product of the 4-acryloyloxymethyl-2-methoxy-2-methyl-1,3-dioxolane was obtained in a yield of 63% by GC analysis.

Workup

  1. customwere metered together into a loop reactor
  2. customThe effluent of the loop reactor within one hour was collected
  3. temperaturecooled

Sources & evidence

ORD record
ord-e1a6fa5c030046dfb3f7edae816e5166
Source dataset
uspto-grants-2007_11
Patent number
US07297812B2

Reaction notes

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