Ethyl bromoacetate → Ethyl 7-methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro-1-naphthaleneacetate

HRID 224963Notes

Reaction equation

HRID 224963 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:14])[CH:10]2[CH3:13])=[CH:5][CH:4]=1.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][C:10]1([CH3:13])[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[CH2:7][CH2:8][C:9]1=[O:14])[CH3:21]

Participants

3

Reactant 2

HCID 7748Ethyl bromoacetateHCID 107977551-Methyl-7-methoxy-2-tetralone

Product 1

HCID 54480711Ethyl 7-methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro-1-naphthaleneacetate

Procedure

The compound 3,4-dihydro-7-methoxy-1-methyl-2(1H)-naphthalenone (VIIIb) (28.23 g, 148 mmol) was reacted with ethyl bromoacetate by the method of Example 5 to yield 36.0 g (88%) (IXb) b.p. 138°-140°/0.1 mm Hg; IR (neat) 1740 cm-1 (unresolved ketone and ester bands); NMR δ, 1.05 and 3.93 (triplet and quartet for CO2CH2CH3), 1.37 (s, 3, CH3), 3.80 (s, 3, OCH3), 6.6-7.3 (m, 3, ArH). The distillate crystallized on standing. A sample recrystallized from ethanol melted at 55°-55.5°.

Workup

  1. customto yield 36.0 g (88%) (IXb) b.p. 138°-140°/0.1 mm Hg
  2. customThe distillate crystallized on standing
  3. customA sample recrystallized from ethanol melted at 55°-55.5°

Sources & evidence

ORD record
ord-fac7b279b51840088aaa41d9eedff059
Source dataset
uspto-grants-1980_11
Patent number
US04234731

Reaction notes

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