Acetyl chloride → 7-Acetyl-6-ethyl-1,1,4,4-tetramethyltetralin

HRID 971961Notes

Reaction equation

HRID 971961 reaction equation
[CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[CH:7][C:8]([CH2:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([CH3:15])([CH3:14])[CH2:4][CH2:3]1.C(Cl)(=[O:19])C.[Cl-].[Al+3].[Cl-].[Cl-].C(C[C:29]([CH3:32])(C)C)(C)C>>[CH3:14][C:5]1([CH3:15])[C:6]2[C:11](=[CH:10][C:9]([CH2:29][CH3:32])=[C:8]([C:12](=[O:19])[CH3:13])[CH:7]=2)[C:2]([CH3:16])([CH3:1])[CH2:3][CH2:4]1.[CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[CH:7][C:8]([CH2:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([CH3:15])([CH3:14])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 66636-Ethyl-1,1,4,4-tetramethyltetralin2×HCID 109072,2,4-TrimethylpentaneHCID 6451240Aluminum(III) Chloride

Product 2

HCID 66636-Ethyl-1,1,4,4-tetramethyltetralinHCID 69307-Acetyl-6-ethyl-1,1,4,4-tetramethyltetralinYield 89%

Procedure

A solution of 1,1,4,4-tetramethyl-6-ethyl-1,2,3,4-tetrahydronaphthalene (528 grams) and acetyl chloride (234 grams) is added over a 31/2 hour period at 70° C. to a well stirred slurry of aluminum chloride (534 grams), 1,1,4,4-tetramethyl-6-ethyl-1,2,3,4-tetrahydronaphthalene (1200 grams) and isooctane (432 grams). The reaction is worked up as in Example I to afford 689 grams of 1,1,4,4-tetramethyl-6-ethyl-7-acetyl-1,2,3,4-tetrahydronaphthalene (89% based on consumed 1,1,4,4-tetramethyl-6-ethyl-1,2,3,4-tetrahydronaphthalene) and 1106 grams of recovered 1,1,4,4-tetramethyl-6-ethyl-1,2,3,4-tetrahydronaphthalene.

Sources & evidence

ORD record
ord-6c4d0721c4bf4038980ed0710cf35b69
Source dataset
uspto-grants-1979_07
Patent number
US04162256

Reaction notes

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