Tetralin → HCID 20360643, compound
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
Procedure
100.8 g (1.2 mols) of diketene were added dropwise at -30°C to 0.5 1 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 1 of icewater. After extraction with methylene chloride, wahing with water to remove the acid from the organic phase and distillation of the methylene chloride, distillation of the reaction yielded 86 % of acetoacetyl-tetrahydronaphthalene boiling at 135°C under 0.5 torr 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
- additionwere dropped in
- stirringthe reaction mixture was stirred into 3 1 of icewater
- extractionAfter extraction with methylene chloride
- customto remove the acid
- distillationfrom the organic phase and distillation of the methylene chloride, distillation of the reaction
Sources & evidence
- ORD record
- ord-722db3be5b0d41d6b71325a73409ac56
- Source dataset
- uspto-grants-1976_02
- Patent number
- US03937737
Reaction notes
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