Hydrochloric Acid → (Z)-3-(4-(2-methoxyethyl)phenoxy)acrylic acid

HRID 1430173Notes

Reaction equation

HRID 1430173 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:20]=[CH:19][C:8]([O:9]/[CH:10]=[CH:11]\[C:12]([O:14]C(C)(C)C)=[O:13])=[CH:7][CH:6]=1.Cl>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:20]=[CH:19][C:8]([O:9]/[CH:10]=[CH:11]\[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67168776(Z)-tert-butyl 3-(4-(2-methoxyethyl)phenoxy)acrylate

Product 1

HCID 86646353(Z)-3-(4-(2-methoxyethyl)phenoxy)acrylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)/(Z)-tert-butyl 3-(4-(2-methoxyethyl)phenoxy)acrylate (0.57 g) was suspended in a mixture of THF (5 mL)/HCl (2 M, 5 mL) and placed in the microwave reactor (T=100° C., 15 sec). THF was removed by rotary evaporation and the mixture was extracted with CH2Cl2 (10 mL). (E)/(Z)-3-(4-(2-methoxyethyl)phenoxy)acrylic acid was obtained as a white solid after purification by column chromatography using a mixture of hexane/ethyl acetate.

Workup

  1. customplaced in the microwave reactor (T=100° C., 15 sec)
  2. customTHF was removed by rotary evaporation
  3. extractionthe mixture was extracted with CH2Cl2 (10 mL)

Sources & evidence

ORD record
ord-3957423222354393a6352e9a79c75bfc
Source dataset
uspto-grants-2015_01
Patent number
US08940776B2

Reaction notes

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