Phenol → HCID 86615334, 화합물

반응식

[CH2:1]([C:3]1[C:4]([O:21][CH3:22])=[C:5]([CH:9]([CH2:19][CH3:20])[CH2:10][C:11]([C:15]([F:18])([F:17])[F:16])([OH:14])[CH2:12][OH:13])[CH:6]=[CH:7][CH:8]=1)[CH3:2].C(C1C(OC)=C(C(C)C(C)C(C(F)(F)F)(O)CO)C=CC=1)C.C1(O)C=CC=CC=1.[NH4+].[Cl-]>>[CH2:1]([C:3]1[C:4]([O:21][CH3:22])=[C:5]([CH:9]([CH2:19][CH3:20])[CH2:10][C:11]([OH:14])([C:15]([F:16])([F:18])[F:17])[CH:12]=[O:13])[CH:6]=[CH:7][CH:8]=1)[CH3:2]

참가 물질

반응물 4

HCID 996Phenol2회

HCID 25517Ammonium Chloride

HCID 66969544HCID 66969544, 화합물

HCID 66969728HCID 66969728, 화합물

생성물 1

HCID 86615334HCID 86615334, 화합물

실험 절차

2.28 (7.12 mmol) of a mixture of 4-(3-ethyl-2-methoxyphenyl)-2-(trifluoromethyl)-hexane-1,2-diol and 4-(3-ethyl-2-methoxyphenyl)-3-methyl-2-(trifluoromethyl)-pentane-1,2-diol (prepared in analogy to the sequence described in Example 110: acetylation of the corresponding phenol, Fries displacement of the acetyl group, etherification of the phenol, Wittig reaction, ene reaction, reduction of the ester to the alcohol) are reacted conventionally with SO3/pyridine complex (3.4 g, 21.35 mmol). After three-hour stirring at room temperature the reaction mixture is poured onto a mixture of saturated NH4Cl solution and ice. It is extracted three times with diethyl ether. The combined organic extracts are washed twice with brine and dried (Na2SO4). Following removal of the solvent on a rotary evaporator, the residue is purified by means of chromatography. (silica gel, eluent: hexane/ethyl acetate). This gives 2.07 g (91.4%) of a mixture of the two aldehydes.