6-Bromo-7-(methoxymethoxy)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene → 3-(Methoxymethoxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

HRID 398063Notes

Reaction equation

HRID 398063 reaction equation
CC1(C)CC(C)(C)C2C(=C(C)C=C([C:14]([OH:16])=[O:15])C=2)O1.[CH3:19][C:20]1([CH3:37])[CH2:29][CH2:28][C:27]([CH3:31])([CH3:30])[C:26]2[CH:25]=[C:24](Br)[C:23]([O:33][CH2:34][O:35][CH3:36])=[CH:22][C:21]1=2.[Li]C(C)(C)C>>[CH3:36][O:35][CH2:34][O:33][C:23]1[C:24]([C:14]([OH:16])=[O:15])=[CH:25][C:26]2[C:27]([CH3:31])([CH3:30])[CH2:28][CH2:29][C:20]([CH3:37])([CH3:19])[C:21]=2[CH:22]=1

Participants

4

Reactant 3

HCID 108536296-Bromo-7-(methoxymethoxy)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene2×HCID 230017612,2,4,4,8-Pentamethyl-6-chromanoic acid2×HCID 178418306HCID 178418306, compound

Product 1

HCID 158405323-(Methoxymethoxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

Procedure

Using the same procedure as for the synthesis of 2,2,4,4,8-pentamethyl-6-chromanoic acid (Compound A1) but using 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-3-methoxymethoxy-2-bromonaphthalene (Compound J, 722 mg, 2.21 mmol) and 2.86 ml of t-BuLi (4.87 mmol, 1.7 M solution in hexane), the title compound was obtained as a white solid (143 mg).

Sources & evidence

ORD record
ord-60bee041c31845719e29343880958caa
Source dataset
uspto-grants-2003_08
Patent number
US06610744B2

Reaction notes

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