Hydrochloric Acid → 3,5-Diisopropoxybenzoic acid-1G

HRID 883829ノート

反応式

HRID 883829 の反応式
C(OC1C=CC=CC=1C([O-])=O)(C)C.[CH:14]([O:17][C:18]1[CH:19]=[C:20]([CH:27]=[C:28]([O:30][CH:31]([CH3:33])[CH3:32])[CH:29]=1)[C:21]([O:23]C(C)C)=[O:22])([CH3:16])[CH3:15].[OH-].[Li+].Cl>C1COCC1.O>[CH:31]([O:30][C:28]1[CH:27]=[C:20]([CH:19]=[C:18]([O:17][CH:14]([CH3:16])[CH3:15])[CH:29]=1)[C:21]([OH:23])=[O:22])([CH3:33])[CH3:32]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 40493909IsopropoxybenzoateHCID 58261000Isopropyl 3,5-diisopropoxybenzoate

生成物 1

HCID 205341403,5-Diisopropoxybenzoic acid-1G収率 55%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

Crude isopropoxybenzoate from above (compound E) was dissolved in 200 mL THF/H2O (1:1) in a 500 mL flask. Excess lithium hydroxide (10 g) was added and the reaction refluxed for over 48 hours. The mixture was cooled, acidified with HCl to pH 2, then extracted with several portions of diethyl ether. The organic layers were washed with brine, dried over MgSO4, and concentrated to a white solid in 55% yield over 2 steps: IR (cm−1): 3064, 2978, 2933, 2639, 1693, 1594, 1300, 1158, 1114, 1040, 767; 1H NMR (250 MHz, CD3OD): δ 1.30 (dd, J=2.3, 5.9 Hz, 12H), 4.59 (qn, J=6.2 Hz, 2H), 6.61 (t, J=2.3 Hz, 1H), 7.10 (d, J=2.5 Hz, 2H); 13C NMR (63 MHz, CD3OD): 22.2 (4C), 71.2 (2C), 109.8, 109.9, 133.8, 160.3 (2C), 169.7.

後処理

  1. temperaturethe reaction refluxed for over 48 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with several portions of diethyl ether
  4. washThe organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to a white solid in 55% yield over 2 steps

出典と根拠

ORDレコード
ord-2f7927aeaf8d4a39baf3b92ea88b9f84
出典データセット
uspto-grants-2012_08
特許番号
US08237003B2

反応ノート

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