Tetralin → HCID 20360643, compound

HRID 2082790Notes

Reaction equation

HRID 2082790 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.F.[CH2:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1.[CH2:18]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>>[C:4]([CH:16]1[C:17]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13][CH2:14][CH2:15]1)(=[O:5])[CH2:3][C:2]([CH3:1])=[O:6].[C:4]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])(=[O:5])[CH2:3][C:2]([CH3:1])=[O:6]

Participants

6

Reactant 4

HCID 8404TetralinHCID 12661DiketeneHCID 14917Hydrofluoric AcidHCID 31237Dodecylbenzene

Product 2

HCID 19733530HCID 19733530, compoundYield 40%HCID 20360643HCID 20360643, compoundYield 86%

Procedure

100.8 g (1.2 mols) of diketene were added dropwise at -30° C to 0.5 l of anhydrous hydrofluoric acid and a mixture of 0.6 mol of tetrahydronaphthalene and 0.6 mol of commercial grade dodecyl-benzene were dropped in. After stirring for 12 hours at room temperature, the reaction mixture was stirred into 3 l of icewater. After extraction with methylene chloride, washing with water to remove the acid from the organic phase and distillation of the methylene chloride, distillation of the reaction mixture yielded 86 % of acetoacetyl-tetrahydronaphthalene boiling at 135° C under 0.5 terr and 77 g (40%) of acetoacetyl-dodecyl-benzene boiling at 160° C under 0.5 torr as found by gas chromatographic determination of the fractions.

Workup

  1. additionwere dropped in
  2. stirringthe reaction mixture was stirred into 3 l of icewater
  3. extractionAfter extraction with methylene chloride
  4. washwashing with water
  5. customto remove the acid
  6. distillationfrom the organic phase and distillation of the methylene chloride, distillation of the reaction mixture

Sources & evidence

ORD record
ord-e935bf94ff6549bd9d3ebf2a98f8692a
Source dataset
uspto-grants-1978_04
Patent number
US04082807

Reaction notes

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