Acetic Acid → Propylene glycol 1-caprate

HRID 464146

반응식

HRID 464146 반응식
[C:1]([O:12][CH2:13][C:14](=[O:16])[CH3:15])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[BH4-].[Na+].C(O)(=O)C.C(OCC)C>O1CCCC1.C1C=CC=CC=1.C(Cl)(Cl)Cl>[C:1]([O:12][CH2:13][CH:14]([OH:16])[CH3:15])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 137501072-Oxopropyl decanoate

생성물 1

HCID 9816033Propylene glycol 1-caprate수율 98.5%

시약·촉매·용매 3

HCID 241Benzene용매HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

실험 절차

1-Decanoyloxypropan-2-one (44.3 g, 0.194 mole) was dissolved in a solution of tetrahydrofuran (1100 cm3) and benzene (200 cm3). After cooling to 5°, ice water (80 cm3) was added. Sodium borohydride (11 g, 0.291 mole) was added to the stirred solution in small proportions to maintain the temperature at 5°. After addition the reaction was stirred at 5° for 45 minutes and glacial acetic acid (14 cm3) was added dropwise. Stirring at 5° was continued for a further 30 minutes. Diethyl ether and chloroform (200 cm3 each) were added and the mixture washed with water (2×200 cm3), a 1% sodium bicarbonate solution (200 cm3) and brine (200 cm3). The organic phase was dried over sodium sulphate and evaporated to yield 1-decanoyloxypropan-2-ol as a colorless liquid (44.0 g, 0.191 mole, 98%), ir (neat) 3600-3100, 2920, 2860, 1730, 1460, 1375, 1240, 1175, 1110, 1055 cm-1 ; pmr (CDCI3) δ 4.0 (m, 2 H), 3.6 (m, 1 H), (D2) m 1 H), 2.3 (t, 2 H), 2.0-1.0 (bm, 17 H) and 0.85 (t, 3 H) ppm.

후처리

  1. temperatureAfter cooling to 5°
  2. temperatureto maintain the temperature at 5°
  3. additionAfter addition the reaction
  4. stirringStirring at 5°
  5. waitwas continued for a further 30 minutes
  6. washthe mixture washed with water (2×200 cm3)
  7. dry with materialThe organic phase was dried over sodium sulphate
  8. customevaporated

출처 및 근거

ORD 기록
ord-26a6b62f2f134340852aa4d7adf75037
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04546197

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