Hydrochloric Acid → 3-t-Butyl-5-hydroxybenzoic acid

HRID 532410ノート

反応式

HRID 532410 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)[C:5]([OH:7])=[O:6].C([Li])CCC.B(OC)(OC)[O:21]C.[OH-].[Na+].OO.Cl>C1COCC1.O.CC(=O)OCC>[C:11]([C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([OH:21])[CH:10]=1)[C:5]([OH:7])=[O:6])([CH3:14])([CH3:13])[CH3:12]

参加物

10

反応物 6

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 8470Trimethyl borateHCID 14798Sodium HydroxideHCID 210882993-Bromo-5-tert-butylbenzoic acidHCID 178418339Butyllithium

生成物 1

HCID 217986673-t-Butyl-5-hydroxybenzoic acid

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-Bromo-5-tert-butylbenzoic acid (5 g) was dissolved in THF (180 ml), and n-butyllithium (18.7 ml, 2.5 M in hexane) was added dropwise under argon and at −75° C., and stirred for a further 30 min. Then trimethyl borate (6.63 ml) was added dropwise and the mixture was allowed to come to RT within 1 h. Thereafter, sodium hydroxide (0.778 g), dissolved in 2 ml of water, and hydrogen peroxide (12.89 ml, 30%) were added in succession. After stirring at RT for 3 h, the mixture was left to stand over the weekend. Then water and EA were added, the mixture was adjusted to pH 3 with 1 N hydrochloric acid and the EA phase was removed. This phase was washed three times with water, dried, filtered and concentrated. The residue was purified using silica gel (120 g cartridge, n-heptane/MtB ether gradient of 0-50% in 60 min). 1.94 g of the title compound were obtained.

後処理

  1. waitto come to RT within 1 h
  2. stirringAfter stirring at RT for 3 h
  3. waitthe mixture was left
  4. customthe EA phase was removed
  5. washThis phase was washed three times with water
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified
  10. customsilica gel (120 g cartridge, n-heptane/MtB ether gradient of 0-50% in 60 min)

出典と根拠

ORDレコード
ord-8cb451fc121d4d6ab6f41d1318dd83ac
出典データセット
uspto-grants-2014_10
特許番号
US08853206B2

反応ノート

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