Sodium Carbonate → 4-(2,4,6-Trimethylphenyl)benzoic acid

HRID 480523

反応式

HRID 480523 の反応式
[C:1]1([CH3:12])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1B(O)O.Br[C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CC.COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:1]1([CH3:12])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1

参加物

9

反応物 4

HCID 10340Sodium CarbonateHCID 114644-Bromobenzoic acidHCID 11776TriphenylphosphineHCID 2921842,4,6-Trimethylbenzeneboronic acid

生成物 1

HCID 227304674-(2,4,6-Trimethylphenyl)benzoic acid

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 10311-Propanol溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a solution of mesitylboronic acid (10 9) and 4-bromobenzoic acid (12.9 g) in 1-propanol (150 mL) and DME (200 mL) were added triphenylphosphine (0.128 g), 2M sodium carbonate solution (37 mL) and water (30 mL). To the mixture was added palladium acetate (82 mg) under nitrogen atmosphere. The mixture was heated to reflux overnight. After the heat source was removed, 100 mL of water was added and stirred for 2.5 h while cooling to room temperature. The darkened mixture was diluted with 150 mL of ethyl acetate and the two phases were separated. The organic layer was washed several times with saturated sodium bicarbonate solution until TLC indicated that 4-bromobenzoic acid (Rf=0.55, eluant: CH2Cl2/CH3OH=5) was completely removed. The solution was extracted three times with 200 mL of 1N NaOH solution. To the combined aqueous layers was added about 50 mL of 12 N HCl to pH 3. The resultant precipitate were filtered, washed with water, and dried to give 4-Mesitylbenzoic acid as a white solid (8.81g). Rf=0.75 (eluant: CH2Cl2/CH3OH=5) 1H-NMR (300 MHz, CDCl3): δ1.997 (s,6 H), 2.340 (s,3 H), 6.961 (s,2 H), 7.274 (d,J=8.1 Hz,2 H), 8.177 (d,J=8.1Hz,2 H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customAfter the heat source was removed
  4. addition100 mL of water was added
  5. additionThe darkened mixture was diluted with 150 mL of ethyl acetate
  6. customthe two phases were separated
  7. washThe organic layer was washed several times with saturated sodium bicarbonate solution until TLC
  8. customwas completely removed
  9. extractionThe solution was extracted three times with 200 mL of 1N NaOH solution
  10. additionTo the combined aqueous layers was added about 50 mL of 12 N HCl to pH 3
  11. filtrationThe resultant precipitate were filtered
  12. washwashed with water
  13. customdried

出典と根拠

ORDレコード
ord-26290825c98a40c2b855d11577f55212
出典データセット
uspto-grants-2003_11
特許番号
US06652835B1

関連ノート

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