Hydrochloric Acid → [4-(Cyclobutylmethoxy)-3-methoxyphenyl]acetic acid

HRID 391365

反応式

HRID 391365 の反応式
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH:9]1[CH2:12][CH2:11][CH2:10]1.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]CC)=[O:22])=[CH:16][C:15]=1[O:26][CH3:27].[OH-].[Na+].Cl>CC(=O)CC>[CH:9]1([CH2:8][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][C:15]=2[O:26][CH3:27])[CH2:12][CH2:11][CH2:10]1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 108965Ethyl homovanillateHCID 2734658(Bromomethyl)cyclobutane

生成物 1

HCID 25019427[4-(Cyclobutylmethoxy)-3-methoxyphenyl]acetic acid収率 95%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

To a stirred solution of ethyl ethyl (4-hydroxy-3-methoxyphenyl)acetate (1.05 g, 5.0 mmol) and potassium carbonate (1.38 g, 10 mmol) in 40 mL of 2-butanone at ambient temperature was added in one portion of (bromomethyl)cyclobutane (97% pure) (1.53 g, 10.0 mmol). The stirred reaction mixture was heated at reflux for 24 hr. HPLC revealed the disappearance of the starting material of ethyl (4-hydroxy-3-methoxyphenyl)acetate. The mixture was allowed to cool to ambient temperature. The solid was filtered off. The filter cake was washed with acetone. The combined filtrate was concentrated in vacuo to nearly dryness. Methanol was added (5 mL) was added to the residue, followed by the addition of a 2-N aqueous solution of NaOH (20 mL, 40 mmol). The reaction was stirred overnight at about 40° C. HPLC indicated that the saponification was completed, and revealed one single peak signal of the expected carboxylic acid. The reaction mixture was subjected to roto-vaporation to remove methanol. Ice was added to the basic aqueous solution. The acidification with a 25 mL of HCl aqueous 2N solution (50 mmol) led to the immediate precipitation of a white solid. Stirring was continued for an additional 30 min and then the precipitation was filtered off with suction through a sintered glass funnel. The collected solid was successively washed with three 50-mL portions of water, and two 25-mL portions of hexane. The collected solid was dried in vacuo for two days at ambient temperature to afford 1.20 g (95%) of [4-(cyclobutylmethoxy)-3-methoxyphenyl]acetic acid as a white solid.

後処理

  1. customThe stirred reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 24 hr
  4. filtrationThe solid was filtered off
  5. washThe filter cake was washed with acetone
  6. concentrationThe combined filtrate was concentrated in vacuo to nearly dryness
  7. additionMethanol was added (5 mL)
  8. additionwas added to the residue
  9. customto remove methanol
  10. additionIce was added to the basic aqueous solution
  11. stirringStirring
  12. waitwas continued for an additional 30 min
  13. customthe precipitation
  14. filtrationwas filtered off with suction through a sintered glass funnel
  15. washThe collected solid was successively washed with three 50-mL portions of water, and two 25-mL portions of hexane
  16. customThe collected solid was dried in vacuo for two days at ambient temperature

出典と根拠

ORDレコード
ord-49ca8d43f8e14ae2862cd39b69bd1879
出典データセット
uspto-grants-2013_02
特許番号
US08383852B2

関連ノート

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