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Hydrochloric Acid → 2-(4-Tert-butyl-2,6-dimethylphenyl)acetic acid

HRID 1183852
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HRID 1183852 반응식
[C:1]([C:5]1[CH:15]=[C:14]([CH3:16])[C:8]([CH:9](O)[C:10]([OH:12])=[O:11])=[C:7]([CH3:17])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.C(C1C=C(C)C(C(O)C(O)=O)=C(C)C=1)(C)(C)C.Cl>C(O)(=O)C>[C:1]([C:5]1[CH:6]=[C:7]([CH3:17])[C:8]([CH2:9][C:10]([OH:12])=[O:11])=[C:14]([CH3:16])[CH:15]=1)([CH3:4])([CH3:3])[CH3:2]
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 529158312-(4-(Tert-butyl)-2,6-dimethylphenyl)-2-hydroxyacetic acidHCID 674987574-tert-Butyl-2,6-dimethylmandelic acid acetate

생성물 1

HCID 529158172-(4-Tert-butyl-2,6-dimethylphenyl)acetic acid수율 86%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

A mixture of 2.89 g of 4-tert-butyl-2,6-dimethylmandelic acid and 7.75 g of 4-tert-butyl-2,6-dimethylmandelic acid acetate, 4.5 g of 37% strength hydrochloric acid, 1.86 g of red phosphorus and 0.66 g of KI in 30 ml of glacial acetic acid is heated at 100° C. for 16 hours. Excess phosphorus is filtered off with suction and washed three times with in each case 10 ml of glacial acetic acid. The filtrate is substantially concentrated on a rotary evaporator at a bath temperature of 50° C./60 mbar. The resulting residue is diluted with 25 ml of water and, by addition of 10% strength aqueous sodium hydroxide solution, dissolved. This solution is extracted twice with in each case 20 ml of MTBE and then adjusted to pH 1 using 48% strength sulfuric acid. The resulting greasy solid is taken up in methylene chloride. This solution is extracted with 25 ml of water, dried over sodium sulfate and concentrated using a rotary evaporator. This gives 7.66 g of 4-tert-butyl-2,6-dimethylphenylacetic acid in a purity of 99.0 GC area % (yield about 86% of theory).

후처리

  1. filtrationExcess phosphorus is filtered off with suction
  2. washwashed three times with in each case 10 ml of glacial acetic acid
  3. concentrationThe filtrate is substantially concentrated on a rotary evaporator at a bath temperature of 50° C./60 mbar
  4. additionThe resulting residue is diluted with 25 ml of water and, by addition of 10% strength aqueous sodium hydroxide solution
  5. dissolutiondissolved
  6. extractionThis solution is extracted twice with in each case 20 ml of MTBE
  7. extractionThis solution is extracted with 25 ml of water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customa rotary evaporator

출처 및 근거

ORD 기록
ord-b828432b47e24fc0a694b0f4dbe5d9a0
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08664428B2

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