Sodium Hydroxide → 4-[1-(4'-Tertbutyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoic acid

HRID 1160902ノート

反応式

HRID 1160902 の反応式
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:6][CH:5]=1.[OH-].[Na+]>C(O)C>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([C:19]2[CH:20]=[CH:21][C:16]([O:15][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:32])=[O:2])=[CH:9][CH:8]=3)[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:17][CH:18]=2)=[CH:27][CH:26]=1)([CH3:30])([CH3:31])[CH3:29]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 671535394-[1-(4'-Tertbutyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoic acid methyl ester

生成物 1

HCID 671535284-[1-(4'-Tertbutyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of racemic 4-(1-hydroxy-3-methyl-butyl)-benzoic acid methyl ester (300 mg, 1.35 mmol) in toluene (14 mL) is added 1,1′-(azodicarbonyl)dipiperidine (ADDP, 512 mg, 2.03 mmol) at 0° C., followed by the addition of tributylphosphine (0.5 mL, 2.03 mmol) and 4′-tert butyl-biphenyl-4-ol (367 mg, 1.62 mmol). The reaction mixture is warmed up to room temperature and stirred overnight. The mixture is loaded on silica gel, eluted with hexanes with a gradient from 0% of ethyl acetate to 50% of ethyl acetate giving 4-[1-(4′-tertbutyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoic acid methyl ester. The ester product is taken into ethanol (5 mL), treated with sodium hydroxide (5N aqueous, 1 mL) for 3 h at room temperature. The mixture is concentrated, diluted with ethyl acetate, acidified with 5 N HCl (1 mL), extract with ethyl acetate. The organic layers are dried and concentrated giving 4-[1-(4′-tertbutyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoic acid (400 mg).

後処理

  1. concentrationThe mixture is concentrated
  2. additiondiluted with ethyl acetate
  3. extractionextract with ethyl acetate
  4. customThe organic layers are dried
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-82a3941fd6184d83995ef1393eecb58c
出典データセット
uspto-grants-2010_10
特許番号
US07816557B2

反応ノート

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