Anisole → 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 2171732Notes

Reaction equation

HRID 2171732 reaction equation
CC(O)(CCC(C)(O)C)C.C1(OC)C=CC=CC=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[C:27]([CH3:32])([CH3:31])[CH2:26][CH2:25][C:24]2([CH3:34])[CH3:33].B(Br)(Br)Br>C(Cl)Cl>[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[C:27]([CH3:32])([CH3:31])[CH2:26][CH2:25][C:24]2([CH3:34])[CH3:33].[CH3:31][C:27]1([CH3:32])[CH2:26][CH2:25][C:24]([CH3:34])([CH3:33])[C:23]2[CH:22]=[C:21]([OH:20])[CH:30]=[CH:29][C:28]1=2

Participants

7

Reactant 4

HCID 7519AnisoleHCID 80312,5-Dimethyl-2,5-hexanediolHCID 25134Boron tribromideHCID 103310036-Methoxy-1,1,4,4-tetramethyl-2,3-dihydronaphthalene

Product 2

HCID 2687865,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-olHCID 103310036-Methoxy-1,1,4,4-tetramethyl-2,3-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Methoxy-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene was prepared employing the procedures described in U.S. Pat. Appl. Publ. 2005/0148590 A1, employing 2,5-dimethyl-hexane-2,5-diol and anisole as the starting materials. 6-Methoxy-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene was subsequently treated with BBr3 in CH2Cl2 to provide the title compound.

Sources & evidence

ORD record
ord-c3299d83fb3a44d98ca1a52a48efe378
Source dataset
uspto-grants-2015_06
Patent number
US09051331B2

Reaction notes

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