3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid → 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid 4-bromobutyl ester

HRID 1072266Notes

Reaction equation

HRID 1072266 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[O:13][CH3:14].[CH2:15]1[CH2:19]O[CH2:17][CH2:16]1.C(Br)(Br)(Br)[Br:21]>>[Br:21][CH2:17][CH2:16][CH2:15][CH2:19][O:11][C:10](=[O:12])[CH:9]=[CH:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:13][CH3:14])[CH:4]=1

Participants

4

Reactant 3

HCID 7093-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic AcidHCID 8028TetrahydrofuranHCID 11205Carbon tetrabromide

Product 1

HCID 539389163-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid 4-bromobutyl esterYield 265.4%

Procedure

To a solution of 3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid (10 g, 51.5 mmoles) in THF (400 ml) triphenylphosphine (2.7 g, 10.3 mmoles) and carbon tetrabromide (34.16 g, 10.3 mmoles) are added and the solution is left at room temperature, under magnetic stirring, for 48 hours. The solid is filtered and then evaporated at reduced pressure. The obtained crude product is purified by chromatography on silica gel eluting with n-hexane/ethyl acetate 7/3. 9 g of 3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 4-bromobutyl ester are obtained. M.p.=86-89° C.

Workup

  1. filtrationThe solid is filtered
  2. customevaporated at reduced pressure
  3. customThe obtained crude product
  4. customis purified by chromatography on silica gel eluting with n-hexane/ethyl acetate 7/3

Sources & evidence

ORD record
ord-e4651da3442444abae41ab52c4a87d9d
Source dataset
uspto-grants-2005_06
Patent number
US06909007B1

Reaction notes

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