Hydrochloric Acid → 2,3,5,6-Tetrafluoro-4-hydroxymethylbenzoic Acid

HRID 2421583

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HRID 2421583 반응식
[BH4-].[Na+].[F:3][C:4]1[C:12]([F:13])=[C:11]([C:14](O)=[O:15])[C:10]([F:17])=[C:9]([F:18])[C:5]=1[C:6]([OH:8])=[O:7].Cl.FC1(CO)C(F)=CC(F)=C(F)C1CO>O.C1(C)C=CC=CC=1.C(COC)OC>[C:6]([C:5]1[C:9]([F:18])=[C:10]([F:17])[C:11]([CH2:14][OH:15])=[C:12]([F:13])[C:4]=1[F:3])([OH:8])=[O:7]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 695492,3,5,6-Tetrafluoroterephthalic acidHCID 4311764Sodium borohydrideHCID 667129532,3,5,6-Tetrafluorobenzenedimethanol2회

생성물 1

HCID 866451092,3,5,6-Tetrafluoro-4-hydroxymethylbenzoic Acid수율 29%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 80711,2-Dimethoxyethane용매2회

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온도
50 °C

실험 절차

Into a 200 ml flask, 2.58 g of sodium borohydride and 25 g of dimethoxyethane were charged at room temperature and the obtained mixture was heated to 50° C. A mixed solution of 6.1 g of 2,3,5,6-tetrafluoroterephthalic acid and 20 g of dimethoxyethane was added dropwise to the mixture over 1 hour while stirring at the same temperature to effect the reaction for 7 hours at 60° C. After adding 25 g of toluene to the reaction mixture and cooling the obtained mixture at 25° C., 8.5 g of 35% by weight aqueous hydrochloric acid was added thereto dropwise over 1 hour at 25 to 30° C. and the resultant mixture was stirred and kept for 6 hours at 25 to 30° C. To the obtained mixture, 30 g of water was added. After leaving the mixture at rest, the mixture was separated to an organic layer and an aqueous layer. The aqueous layer was extracted twice with 30 g of ethyl acetate and the obtained oil layers were mixed with the organic layer previously obtained. The organic layer after mixing was washed with 10 g of a saturated potassium carbonate and then 10 g of water, and the organic layer was concentrated to obtain the solid containing 2,3,5,6-tetrafluorobenzenedimethanol. The yield of 2,3,5,6-tetrafluorobenzenedimethanol was 33%. Alternatively, 4-carboxy-2,3,5,6-tetrafluorobenzyl alcohol was formed as by-products in the yield of 29%, and a raw material 2,3,5,6-tetrafluoroterephthalic acid remained in 38%.

후처리

  1. customthe reaction for 7 hours at 60° C
  2. temperaturecooling the obtained mixture at 25° C.
  3. waitkept for 6 hours at 25 to 30° C
  4. customAfter leaving the mixture at rest
  5. customthe mixture was separated to an organic layer
  6. extractionThe aqueous layer was extracted twice with 30 g of ethyl acetate
  7. additionthe obtained oil layers were mixed with the organic layer
  8. custompreviously obtained
  9. additionThe organic layer after mixing
  10. washwas washed with 10 g of a saturated potassium carbonate
  11. concentration10 g of water, and the organic layer was concentrated
  12. customto obtain the solid

출처 및 근거

ORD 기록
ord-8516a1fb361a441aa1445db052600d82
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07956223B2

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