Hydrochloric Acid → 4-(2-Methoxyethoxy)-3-methylbenzoic acid

HRID 713010

反応式

HRID 713010 の反応式
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].[OH-].C([P+](CCCC)(CCCC)CCCC)CCC.Br[CH2:31][CH2:32][O:33][CH3:34].Cl>C1COCC1>[CH3:34][O:33][CH2:32][CH2:31][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 681384-Hydroxy-3-methylbenzoic acidHCID 809722-Bromoethyl methyl etherHCID 84487Phosphonium, tetrabutyl-, hydroxide (1:1)

生成物 1

HCID 585513704-(2-Methoxyethoxy)-3-methylbenzoic acid収率 6.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4-hydroxy-3-methyl-benzoic acid (2.0 g, 13 mmol) in THF (24 mL) was added tetrabutylphosphonium hydroxide (18 mL of 40% w/v, 26 mmol). The reaction mixture was cooled to 0° C. and then 1-bromo-2-methoxy-ethane (1.8 g, 1.2 mL, 13 mmol) was added. The reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was acidified using 1M HCl and the aqueous layer was extracted with ethyl acetate. The organics were dried over sodium sulfate and concentrated in vacuo to yield 4-(2-methoxyethoxy)-3-methylbenzoic acid (182 mg, 6%). ESI-MS m/z calc. 210.2. found 209.2 (M-H)−; Retention time: 0.96 minutes (3 min run).

後処理

  1. temperatureto warm to room temperature overnight
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe organics were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ce1380b974c74493b1c2bcf337f5aad9
出典データセット
uspto-grants-2015_11
特許番号
US09181273B2

関連ノート

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