Hydrochloric Acid → 4-(3-Bromophenoxy)butanoic acid

HRID 885998ノート

反応式

HRID 885998 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][CH2:6][CH2:7][CH2:8][C:9]([O:11]CC)=[O:10].O.Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 22407915Ethyl 4-(3-bromophenoxy)butanoate

生成物 1

HCID 23844144-(3-Bromophenoxy)butanoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

Ethyl 4-(3-bromophenoxy)butanoate 6 from Example 5 was taken up in 100 mL THF and 50 mL water and treated with lithium hydroxide LiOH (hydrate, 4.9 g). see FIG. 1. The whole was heated at 50° C. for 2 days. The mixture was cooled to room temperature and acidified to pH 1 with 2N HCl. The aqueous was extracted with ethylacetate. The combined organics were washed with brine and dried over sodium sulfate to give crude 4-(3-Bromophenoxy)butanoic acid as a sticky solid. 1H NMR (DMSO-d6, 500 MHz) 7.24 (m, 1H), 7.13 (m, 1H), 7.11 (m, 1H), 6.95 (m, 1H), 3.99 (m, 2H), 2.37 (m, 2H), 1.94 (m, 2H).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe aqueous was extracted with ethylacetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate

出典と根拠

ORDレコード
ord-d108738887a44f728b29f96700c594e9
出典データセット
uspto-grants-2012_08
特許番号
US08242104B2

反応ノート

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