Citric Acid → 6-(7-Hydroxyheptyl)-7-(3-hydroxy-4-methyloct-1-enyl)-1,4-dioxaspiro[4,4]nonane

HRID 372051ノート

反応式

HRID 372051 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:17]([CH:18]=[CH:19][C:20](=[O:27])[CH:21]([CH3:26])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:16][CH2:15][C:10]21[O:14][CH2:13][CH2:12][O:11]2.C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O.[Na+].[Na+].[Na+].[BH4-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[Cl-].[Na+]>CO.CC(C)=O>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:17]([CH:18]=[CH:19][CH:20]([OH:27])[CH:21]([CH3:26])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:16][CH2:15][C:10]21[O:14][CH2:13][CH2:12][O:11]2

参加物

8

反応物 5

HCID 311Citric AcidHCID 5234Sodium ChlorideHCID 6224Trisodium citrateHCID 4192641Potassium borohydride2 回HCID 570760486-(7-Hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane

生成物 1

HCID 570090666-(7-Hydroxyheptyl)-7-(3-hydroxy-4-methyloct-1-enyl)-1,4-dioxaspiro[4,4]nonane収率 59.7%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 887Methanol溶媒

実験手順

6-(7-Hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane [1.0 g.; prepared as hereinbefore described in Example 1 (v)] was dissolved in methanol (50 ml.) and added to aqueous sodium citrate solution (130 ml.; 2% w/v. To this stirred solution, at -5° to 0° C, solid potassium borohydride (2.24 g.) was added portionwise at such a rate as to avoid undue effervescence and the reaction mixture was maintained at pH 8 by the occasional addition of aqueous citric acid solution (10% w/v). After the final addition of the potassium borohydride the reaction mixture was stirred at -5° to 0° C. and pH 8 for 90 minutes. Acetone (50 ml.) was then added, the solution was saturated with sodium chloride, and extracted with diethyl ether. The combined ether extracts were washed with a saturated solution of sodium chloride in hydrochloric acid (2N) and saturated sodium chloride solution respectively, then dried over sodium sulphate. Removal of the solvent under reduced pressure gave crude 6-(7-hydroxyheptyl)-7-(3-hydroxy-4-methyloct-1-enyl)-1,4-dioxaspiro[4,4]nonane (0.6 g.), νmax 3400 cm-1, 1040 cm-1, 970 cm-1, which was used in the next stage without further purification.

後処理

  1. extractionextracted with diethyl ether
  2. washThe combined ether extracts were washed with a saturated solution of sodium chloride in hydrochloric acid (2N) and saturated sodium chloride solution respectively
  3. dry with materialdried over sodium sulphate
  4. customRemoval of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-f3949e9abaf447579f932fb5fea9236b
出典データセット
uspto-grants-1978_05
特許番号
US04088695

反応ノート

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